2140-72-9

Basic information

• Product Name: 2'-O-Methylcytidine
• Synonyms: 2'-OMe-C;4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-3-methoxy-5-methylol-tetrahydrofuran-2-yl]pyrimidin-2-one;4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidin-2-one;4-azanyl-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-oxolan-2-yl]pyrimidin-2-one;2'-OMe Cytidine;4-aMino-1-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)-3-Methoxyoxolan-2-yl]-1,2-dihydropyriMidin-2-one;2'-O-Methylcytidine, >=99%;2'-O-METHYLCYTIDINE
• CAS NO: 2140-72-9
• Molecular Formula: C₁₀H₁₅N₃O₅
• Molecular Weight: 257.24
• EINECS: 2017-001-1
• Product Categories: Nucleosides, Nucleotides, Oligonucleotides;Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Nucleotides;Biochemicals and Reagents;Nucleoside Analogs
• Mol File: 2140-72-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 252-253 C
• Boiling Point: 506 °C at 760 mmHg
• Flash Point: 259.8 °C
• Appearance: White to Off-white/Powder
• Density: 1.68 g/cm³
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO.
• PKA: 13.37±0.70(Predicted)
• CAS DataBase Reference: 2'-O-Methylcytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-O-Methylcytidine(2140-72-9)
• EPA Substance Registry System: 2'-O-Methylcytidine(2140-72-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2140-72-9(Hazardous Substances Data)

Usage

Description

2'-O-Methylcytidine is a cytidine analog that is modified with a methyl group at the 2' position of the ribose sugar. It is a white powder and is used in the preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

Uses

Used in Pharmaceutical Industry:
2'-O-Methylcytidine is used as a nucleoside derivative for the development of antiviral agents targeting RNA-dependent RNA viral polymerase. This application is crucial in the treatment and prevention of viral infections, particularly those caused by RNA viruses.
Used in Research and Development:
As a cytidine analog, 2'-O-Methylcytidine is utilized in research and development for studying the structure, function, and mechanisms of RNA and DNA molecules. It aids in understanding the role of modified nucleosides in various biological processes and their potential applications in medicine and biotechnology.

Synthetic route

3',5'-di-O-acetyl-2'-O-methylcytidine (1085342-86-4) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With ammonia In methanol at 20℃;	99%

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine (97626-19-2) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	96%

N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine (73793-16-5) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With ammonia In methanol at 4℃; for 48h;	80%

magnesium ethylate (2414-98-4) + 2,2'-anhydrocytidine hydrochloride → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In methanol for 5h; Reflux;	76%

diazomethane (186581-53-3, 908094-01-9) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With tin(ll) chloride In methanol; 1,2-dimethoxyethane for 0.333333h; Ambient temperature;	A 14% B 69%
dibutyldimethoxytin In methanol Mechanism;
dibutyldimethoxytin In methanol

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9) + N3-methylcytidine (2140-64-9)

Conditions	Yield
With copper acetylacetonate In N,N-dimethyl-formamide at 70℃; for 1h;	A 22% B 60% C 3%
In N,N-dimethyl-formamide at 70℃; for 1h;	A 7% B 28% C 13%
With copper acetylacetonate In N,N-dimethyl-formamide at 70℃; for 1h; Product distribution; without metallo-organic compound;
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Title compound not separated from byproducts;	A 7 % Spectr. B 28 % Spectr. C 13 % Spectr.
In methanol; N,N-dimethyl-formamide at 70℃; Title compound not separated from byproducts;	A n/a B 28 % Spectr. C 13 % Spectr.

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With magnesium(II) acetylacetonate In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Product distribution; absence of metal ion;	A 2% B 43%
With magnesium(II) acetylacetonate In methanol; N,N-dimethyl-formamide at 70℃; for 1h;	A 2% B 43%

trimethylphenylammonium hydroxide (1899-02-1) + CYTIDINE (65-46-3) → 3-methyluridine (2140-69-4) + 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃;	A n/a B 3 % Spectr. C 24%
In N,N-dimethyl-formamide at 100℃;	A 22 % Spectr. B 4 % Spectr. C 21%

1-methyl-1-nitrosourea (684-93-5) + CYTIDINE (65-46-3) → 2'-O-methylcytidine (2140-72-9) + N3-methylcytidine (2140-64-9)

Conditions	Yield
With borax In water; formamide at 50℃; for 18h;	A 5% B n/a

CYTIDINE (65-46-3) + methyl iodide (74-88-4) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With sodium hydride 1) DMF, 0 deg C, 45 min, 2a) 0 deg C, 2.5 h, 2b) r.t., 1 h; Multistep reaction. Yields of byproduct given;
With sodium hydride 1) DMF, 0 deg C, 45 min, 2a) 0 deg C, 2.5 h, 2b) r.t., 1 h; Yield given. Multistep reaction;

N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-3-methyl-butyramide → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With dichloro-acetic acid; ammonium hydroxide

Trimethyl borate (121-43-7) + 2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate (10212-28-9) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With methanol; boron trifluoride for 48h; Ring cleavage; Heating;

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-4-(2-nitrophenyl)-2-pyrimidinone (108782-90-7) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / silver oxide / acetone / 72 h / 20 °C 2: 75 percent / ammonia / tetrahydrofuran 3: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-2'-O-methyl-4-(2-nitrophenyl)-2-pyrimidinone (110567-19-6) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / ammonia / tetrahydrofuran 2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

4-(2-Nitro-phenoxy)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 2: 81 percent / silver oxide / acetone / 72 h / 20 °C 3: 75 percent / ammonia / tetrahydrofuran 4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine (415903-48-9) → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 2: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 3: 81 percent / silver oxide / acetone / 72 h / 20 °C 4: 75 percent / ammonia / tetrahydrofuran 5: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

uridine (58-96-8) + aqueous H3PO4 → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: pyridine / 20 °C 2: triethylamine / CH2Cl2 / 0.25 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 4: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 5: 81 percent / silver oxide / acetone / 72 h / 20 °C 6: 75 percent / ammonia / tetrahydrofuran 7: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: triethylamine / CH2Cl2 / 0.25 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 3: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 4: 81 percent / silver oxide / acetone / 72 h / 20 °C 5: 75 percent / ammonia / tetrahydrofuran 6: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose (68045-07-8) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) HMDS, (NH4)2SO4, 2.) SnCl4 / 1.) reflux, overnight, 2.) dichloroethane, reflux, 60 min 2: 80 percent / NH3 / methanol / 48 h / 4 °C View Scheme

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / BF3*(C2H5)2O / CH2Cl2 / 0 °C 2: 1.) HMDS, (NH4)2SO4, 2.) SnCl4 / 1.) reflux, overnight, 2.) dichloroethane, reflux, 60 min 3: 80 percent / NH3 / methanol / 48 h / 4 °C View Scheme

methanol-dichloromethane + CYTIDINE (65-46-3) + methyl iodide (74-88-4) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In N-methyl-acetamide; methanol; ethanol; dichloromethane

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-methylcytidine (2140-72-9) → 5'-O-(tert-butyldimethylsilyl)-2'-O-methylcytidine (1171006-87-3)

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine at 20℃;	100%
With pyridine at 20℃;

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + 2'-O-methylcytidine (2140-72-9) → 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine (97626-19-2)

Conditions	Yield
With pyridine for 1h; Ambient temperature;	98%

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-methylcytidine (2140-72-9) → 3',5'-O-bis(tert-butyldimethylsilyl)-2'-O-methylcytidine (367511-42-0)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;	97.5%

2'-O-methylcytidine (2140-72-9) → 5-bromo-2'-O-methylcytidine (494210-77-4)

Conditions	Yield
With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 1.5h;	78%

trimethylsulphonium iodide (2181-42-2) + 2'-O-methylcytidine (2140-72-9) → 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one (120057-51-4)

Conditions	Yield
In N,N-dimethyl-formamide at 85℃; for 3.5h; Rate constant; Product distribution; Mechanism; other nucleosides and trimethylsulphonium hydroxide;	67%
In N,N-dimethyl-formamide at 85℃; for 3.5h;	67%

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester (1337529-56-2) + 2'-O-methylcytidine (2140-72-9) → C22H31N4O9P

Conditions	Yield
Stage #1: 2'-O-methylcytidine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: (S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere;	16.3%

benzoic acid anhydride (93-97-0) + 2'-O-methylcytidine (2140-72-9) → 2'-O-methyl-N4-benzoylcytidine (52571-45-6)

Conditions	Yield
In ethanol for 1h; Heating;	0.38 g

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 2'-O-methylcytidine (2140-72-9) → 2'-O-methyl-4-N-(9-fluorenylmethoxycarbonyl)cytidine (135944-10-4)

Conditions	Yield
Yield given. Multistep reaction;

trimethylsulphonium hydroxide (17287-03-5) + 2'-O-methylcytidine (2140-72-9) → 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one (120057-51-4) + N4,O2'-dimethylcytidine (13048-95-8) + O2',O3'-dimethyl-cytidine (34218-86-5)

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Title compound not separated from byproducts;	A 34 % Spectr. B 21 % Spectr. C 8 % Spectr.

2'-O-methylcytidine (2140-72-9) → 5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine (86872-24-4)

Conditions	Yield
Multistep reaction;

chloro-trimethyl-silane (75-77-4) + 2'-O-methylcytidine (2140-72-9) → 4-Amino-1-((2R,3R,4R,5R)-3-methoxy-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

Conditions	Yield
In pyridine 0 deg C -> r.t. for 1-2 h;
With pyridine Silylation;

acetic anhydride (108-24-7) + 2'-O-methylcytidine (2140-72-9) → N4-acetyl-2'-O-methyl cytidine (113886-71-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Acetylation;	0.94 g

2'-O-methylcytidine (2140-72-9) → 5-bromo-3'-O-[(tert-butyldimethyl)silyl]-2'-O-methylcytidine (444019-26-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: 83 percent / LiBr; ammonium ceric(IV) nitrate / acetonitrile / 3 h / 20 °C 3: 40 percent / aq. AcOH / 6 h / 50 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 5-bromo-3',5'-O-bis[(tert-butyldimethyl)silyl]-2'-O-methylcytidine (848860-93-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: 83 percent / LiBr; ammonium ceric(IV) nitrate / acetonitrile / 3 h / 20 °C View Scheme

2'-O-methylcytidine (2140-72-9) → N4-(4,4'-dimethoxytrityl)-2'-O-methylcytidine (444019-24-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: DMAP; pyridine / 20 °C 3: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 2,2-dimethyl-thiopropionic acid S-(2-{[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-yloxy]-[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-phosphoryloxy}-ethyl) ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2.1: DMAP; pyridine / 20 °C 3.1: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C 4.1: 1H-tetrazole / acetonitrile / 20 °C 4.2: 3-chloroperbenzoic acid / CH2Cl2 / 20 °C 4.3: aq. AcOH / methanol / 55 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 2'-O-methylcytidine-5'-[bis-(S-pivaloyl-2-thioethyl)phosphate]

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2.1: DMAP; pyridine / 20 °C 3.1: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C 4.1: 1H-tetrazole / acetonitrile / 20 °C 4.2: 3-chloroperbenzoic acid / CH2Cl2 / 20 °C 4.3: 22 percent / aq. AcOH / methanol / 55 °C View Scheme

Upstream product

• 186581-53-3 diazomethane 
• 65-46-3 CYTIDINE 
• 17287-03-5 trimethylsulphonium hydroxide 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 74-88-4 methyl iodide 
• 69304-38-7 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 1085342-86-4 3',5'-di-O-acetyl-2'-O-methylcytidine 
• 684-93-5 1-methyl-1-nitrosourea 
• 2414-98-4 magnesium ethylate 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 68045-07-8 1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose 
• 58-96-8 uridine 
• 110567-19-6 1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-2'-O-methyl-4-(2-nitrophenyl)-2-pyrimidinone 
• 108782-90-7 1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-4-(2-nitrophenyl)-2-pyrimidinone 

Downstream Products

• 52571-45-6 2'-O-methyl-N⁴-benzoylcytidine 
• 110764-74-4 N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-methylcytidine 
• 444019-24-3 N⁴-(4,4'-dimethoxytrityl)-2'-O-methylcytidine 
• 113886-71-8 N⁴-acetyl-2'-O-methyl cytidine 
• 86872-24-4 5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine 
• 120057-51-4 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one 
• 13048-95-8 N4,2'-O-dimethylcytidine 
• 34218-86-5 O^2'_,O3'-dimethyl-cytidine 

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