75985-45-4

Basic information

• Product Name: 2-PYRIMIDINEMETHANAMINE
• Synonyms: RARECHEM AL BW 0784;PYRIMIDIN-2-YL-METHYLAMINE;C-PYRIMIDIN-2-YL-METHYLAMINE;2-PYRIMIDINEMETHANAMINE;2-Pyrimidinemethanamine (9CI);C-PyriMidin-2-yl-MethylaMine, fuMMerate
• CAS NO: 75985-45-4
• Molecular Formula: C₅H₇N₃
• Molecular Weight: 109.13
• EINECS: 1806241-263-5
• Product Categories: PYRIMIDINE;Heterocycle-Pyrimidine series
• Mol File: 75985-45-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 179.9 °C at 760 mmHg
• Flash Point: 83.7 °C
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0.919mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 2-PYRIMIDINEMETHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PYRIMIDINEMETHANAMINE(75985-45-4)
• EPA Substance Registry System: 2-PYRIMIDINEMETHANAMINE(75985-45-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 75985-45-4(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

2-Pyrimidinemethanamine can be prepared to combat abiotic plant stress.

InChI:InChI=1/C5H7N3/c6-4-5-7-2-1-3-8-5/h1-3H,4,6H2

Synthetic route

2-cyanopyrimidine (14080-23-0) → 2-aminomethylpyrimidine (75985-45-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol under 760.051 Torr; for 12h; Inert atmosphere;	95%
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 3h;	44%
With hydrogen; Pd-C; ammonia In ethanol

4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid (330785-84-7) + 2-aminomethylpyrimidine (75985-45-4) → avanafil (330784-47-9)

Conditions	Yield
With dicyclohexyl-carbodiimide; 1-hydroxy-1,2,3-benzotriazine-4(3H)-one In N,N-dimethyl-formamide at 0℃; Temperature;	99%
With 5, 10, 15, 20-tetrakis[4-(dihydroxyboryl)phenyl]-21H,23H-porphine In toluene for 16h; Time; Reflux; Green chemistry;	91.2%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 4h;	90%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; for 8h;

2-methyl-1-(2,6,8-trichloropyrimido[5,4-d]pyrimidin-4-ylamino)propan-2-ol + 2-aminomethylpyrimidine (75985-45-4) → 1-{2,6-dichloro-8-[(pyrimidin-2-ylmethyl)amino]pyrimido[5,4-d]pyrimidin-4-ylamino}-2-methylpropan-2-ol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 70℃; for 2h;	97%

(3-chloro-4-methoxyphenyl)methanamine (115514-77-7) + C6H6N2O5S + 2-aminomethylpyrimidine (75985-45-4) → 4-[(3-chloro-4-methoxybenzyl)amino]-2-methanesulfonyl-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide

Conditions	Yield
Stage #1: C6H6N2O5S With N-ethyl-N,N-diisopropylamine; trichlorophosphate In toluene Reflux; Stage #2: 2-aminomethylpyrimidine With N-ethyl-N,N-diisopropylamine In toluene at -8℃; Stage #3: (3-chloro-4-methoxyphenyl)methanamine With N-ethyl-N,N-diisopropylamine In toluene at 0℃; Temperature;	93.8%

C18H21ClN4O4 + 2-aminomethylpyrimidine (75985-45-4) → C23H26ClN7O3

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	92%

6-(3-chloro-4-methoxy - benzyl-amino)-2 (2-hydroxymethyl-pyrrolidinyl) pyrimidine-5-carboxylic acid + 2-aminomethylpyrimidine (75985-45-4) → C23H28ClN7O3

Conditions	Yield
Stage #1: 6-(3-chloro-4-methoxy - benzyl-amino)-2 (2-hydroxymethyl-pyrrolidinyl) pyrimidine-5-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 40 - 50℃; for 3h; Stage #2: 2-aminomethylpyrimidine In N,N-dimethyl-formamide at 60 - 70℃;	90%

C14H14ClN3O5S + 2-aminomethylpyrimidine (75985-45-4) → 4-[(3-chloro-4-methoxybenzyl)amino]-2-methanesulfonyl-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide

Conditions	Yield
Stage #1: C14H14ClN3O5S With thionyl chloride; N,N-dimethyl-formamide In toluene Reflux; Green chemistry; Stage #2: 2-aminomethylpyrimidine With triethylamine In toluene at 0℃; Green chemistry;	89.5%

Upstream product

• 14080-23-0 2-cyanopyrimidine 

Downstream Products

• 330784-47-9 avanafil 

Relevant articles and documents

MANUFACTURING METHOD OF OPTICAL ACTIVE SECONDARY ALCOHOL

PROBLEM TO BE SOLVED: To provide a method for manufacturing optical active secondary alcohol with high optical purity by hydrogenating a substrate carbonyl compound using a ruthenium complex with a specific optical active diphosphine compound and an amine compound of which synthesis is easy as ligands as a catalyst. SOLUTION: The manufacturing method of optical active secondary alcohol including reacting a substrate carbonyl compound (excluding 3-quinuclidinone, a 3-quinuclidinone derivative having a substituent, and ketone having an aromatic hydrocarbon group and a heterocycle) with hydrogen and/or a hydrogen-donating compound in a presence of a ruthenium complex selected from a compound represented by the following general formula (1) RuXYAB (1) [X and Y are same or different, represent a hydrogen atom or an anionic group, A represents optical active diphosphine represented by the general formula (2), and B represents an amine compound represented by the following general formula (3)]. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT

PROCESS FOR PRODUCING OPTICALLY ACTIVE SECONDARY ALCOHOL

[Object] The object of this invention is to provide a method for producing an optically active secondary alcohol at a high optical purity by hydrogenating a substrate carbonyl compound at a high efficiency using as a catalyst a ruthenium complex bearing as a ligand certain optically active diphosphine compound and a readily synthesized amine compound. [Solution] The method of producing an optically active secondary alcohol according to the present invention is characterized in that a substrate carbonyl compound (provided that 3-quinuclidinone, 3-quinuclidinone derivative having a substituent, and a ketone having an aromatic hydrocarbon group and a heterocycle are excluded) is reacted with hydrogen and/or a hydrogen donating compound in the presence of a ruthenium complex selected from the compounds expressed by following general formula (1) RuXYAB (1) [in the general formula (1), X and Y are the same or different from each other and denote a hydrogen atom or an anionic group, A denotes an optically active diphosphine expressed by the general formula (2), B denotes an amine compound expressed by following general formula (3)].

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