4359-87-9

Basic information

• Product Name: 2,4,6-TRICHLORO-5-NITROPYRIMIDINE
• Synonyms: 2,4,6-TRICHLORO-5-NITROPYRIMIDINE;2,4,6-Trichloro-5-nitropyrimidine ,90%;2,4,6-Trichloro-5-nitropyrimidine, tech.;2,4,6-trichloro-5-nitro-pyriMidine 85+%;2,4,6-Trichloro-5-nitropyrimidine≥ 97% (HPLC)
• CAS NO: 4359-87-9
• Molecular Formula: C₄Cl₃N₃O₂
• Molecular Weight: 228.4207
• EINECS: 200-001-2
• Product Categories: pyrimidine;Heterocycle-Pyrimidine series
• Mol File: 4359-87-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 56-58℃
• Boiling Point: 314℃
• Flash Point: 143℃
• Appearance: /
• Density: 1.848
• Vapor Pressure: 0.000909mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: -10.32±0.39(Predicted)
• CAS DataBase Reference: 2,4,6-TRICHLORO-5-NITROPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRICHLORO-5-NITROPYRIMIDINE(4359-87-9)
• EPA Substance Registry System: 2,4,6-TRICHLORO-5-NITROPYRIMIDINE(4359-87-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4359-87-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to pale yellow solid

InChI:InChI=1/C4Cl3N3O2/c5-2-1(10(11)12)3(6)9-4(7)8-2

Synthetic route

5-nitrobarbituric acid (106351-49-9) → 2,4,6-trichloro-5-nitropyrimidine (4359-87-9)

Conditions	Yield
With diethylamine; trichlorophosphate at 0 - 23℃; for 2.5h;	33%

dilituric acid (106351-49-9) → 2,4,6-trichloro-5-nitropyrimidine (4359-87-9)

Conditions	Yield
Stage #1: dilituric acid With N,N-diethylaniline; trichlorophosphate at 20 - 45℃; Inert atmosphere; Stage #2: With water at 5℃; Cooling with ice;	33%
Stage #1: dilituric acid at 20 - 45℃; Ic; Stage #2: With N,N-diethylaniline; trichlorophosphate Inert atmosphere;	33%

dilituric acid (480-68-2) + N,N-diethylaniline (91-66-7) → 2,4,6-trichloro-5-nitropyrimidine (4359-87-9)

Conditions	Yield
With trichlorophosphate at 28 - 45℃;	13%

dilituric acid (480-68-2) → 2,4,6-trichloro-5-nitropyrimidine (4359-87-9)

Conditions	Yield
With N,N-diethylaniline; trichlorophosphate
With N,N-diethylaniline; trichlorophosphate

dilituric acid (106351-49-9) → 2,4,5,6-tetrachloropyrimidine (1780-40-1) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9)

Conditions	Yield
With 2,6-dimethylpyridine; trichlorophosphate at 90℃; for 3h;

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 2,6-dichloro-5-nitropyrimidin-4-amine (31221-68-8)

Conditions	Yield
With ammonia In tetrahydrofuran; ethanol at -70℃; for 0.5h;	97%
With ammonia In tetrahydrofuran; ethanol at -70℃; for 0.5h;	97%
With diethyl ether; ammonia
With ammonia; triethylamine In tetrahydrofuran; methanol at -78 - 0℃; Product distribution / selectivity;

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 2,6-dichloro-5-nitropyrimidin-4-ol

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	92%

morpholine (110-91-8) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 2,6-dichloro-5-nitro-4-morpholinopyrimidine (13923-34-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 14h;	91%
With triethylamine In dichloromethane at 0 - 20℃;	91%
With triethylamine In dichloromethane at 0 - 20℃;	67%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 5-amino-2,4,6-trichloropyrimidine (91322-00-8)

Conditions	Yield
With iron; acetic acid In methanol at 20℃;	89%
With iron; acetic acid In ethanol at 60℃; for 2h;	46%
With ethanol; nickel Hydrogenation;
With hydrogen; Raney-Nickel2800 In ethanol; water at 20℃;

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + bicyclo[1.1.1]pentan-1-amine hydrochloride → N-(bicyclo[1.1.1]pentan-1-yl)-2,6-dichloro-5-nitropyrimidin-4-amine

Conditions	Yield
Stage #1: 2,4,6-trichloro-5-nitropyrimidine; bicyclo[1.1.1]pentan-1-amine hydrochloride In isopropyl alcohol at -78℃; for 0.5h; Stage #2: With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 0.5h;	84%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + 2-fluorobenzylamine (89-99-6) → C11H7Cl2FN4O2

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h;	84%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + Cyclopentamine (1003-03-8) → 2,6-dichloro-N-cyclopentyl-5-nitropyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 2h;	83%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + 2,4-Difluoro-benzylamine (72235-52-0) → C11H6Cl2F2N4O2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 1h;	82%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 1h;	82%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + 1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) → 4-(2,6-dichloro-5-nitro-pyrimidin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1174766-28-9)

Conditions	Yield
With triethylamine In tetrahydrofuran; dichloromethane at 0 - 25℃;	80%

8-oxa-3-aza-bicyclo[3.2.1]octane (280-13-7) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 3-(2,6-dichloro-5-nitropyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (1250867-75-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	80%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 4-chloro-2,6-dimethoxy-5-nitropyrimidine (60331-03-5)

Conditions	Yield
With sodium methylate In methanol for 0.25h;	73%

o-trifluoromethylbenzylamine (3048-01-9) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → C12H7Cl2F3N4O2

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h;	73%
In tetrahydrofuran at 0℃; for 1h;	73%

methanol (67-56-1) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 2,4,6-trimethoxy-5-nitropyrimidine (83356-02-9)

Conditions	Yield
With sodium methylate In methanol for 1h;	66%

3-aminotetrahydrofuran (88675-24-5) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 2,6-dichloro-5-nitro-N-tetrahydrofuran-3-ylpyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 2h; Inert atmosphere;	66%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + ethyl 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)acetate (1265919-24-1) → ethyl 2-(((3aR,4S,6R,6aS)-6-((2,6-dichloro-5-nitropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)acetate

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h;	59%

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (274693-55-9) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → 2-(((3aR,4S,6R,6aS)-6-((2,6-dichloro-5-nitropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 20℃; for 4h;	59%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + (4-fluoro-2-(trifluoromethyl)phenyl)methanamine (202522-22-3) → C12H6Cl2F4N4O2

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h;	58%
In tetrahydrofuran at 0 - 1℃;	58%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + tetrahydro-2H-pyran-4-ylamine monohydrochloride (33024-60-1) → 2,6-dichloro-5-nitro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine (1352625-52-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 2h;	49%

5-methylisoxazol-3-ylamine (1072-67-9) + 2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → N-(2,6-dichloro-5-nitropyrimidin-4-yl)-5-methylisoxazol-3-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 0 - 20℃; for 3h;	49%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + ((3aR,4R,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol (132342-52-0) → ((3aR,4R,6R,6aS)-6-((2,6-dichloro-5-nitropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)methanol

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.333333h;	43%
With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h;	293 mg

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + ((3aR,4R,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol (132342-52-0) → ((3aR,4R,6R,6a5)-6-(2,6-dichloro-5-nitropyrimidin-4-ylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.333333h;	43%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + sodium t-butanolate (865-48-5) → 2,4-di-tert-butoxy-6-chloro-5-nitropyrimidine

Conditions	Yield
In N,N-dimethyl-formamide at -50 - 20℃; for 0.75h;	39%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + ethyl 2-amino-5-chlorobenzoate (63243-75-4) → ethyl 5-chloro-2-[(2,6-dichloro-5-nitropyrimidin-4-yl)amino]benzoate (1542549-21-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20 - 55℃; for 3h; Inert atmosphere;	33%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + [1-(4-amino-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester (1259224-00-4) → tert-butyl 1-(4-(2,6-dichloro-5-nitropyrimidin-4-ylamino)phenyl)cyclobutylcarbamate (1439393-86-8)

Conditions	Yield
In tetrahydrofuran at 15℃; for 0.5h; Inert atmosphere;	31.5%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + benzyl alcohol (100-51-6) → 2,4-bis(benzyloxy)-6-chloro-5-nitropyrimidine (99277-50-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran at -20 - 23℃; for 6h;	31.3%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) + 3,12-diaza-6,9-diazoniadispiro[5.2.5.3]heptadecane dibromide → 3,3'-(2-chloropyrimidine-4,6-diyl)bis-3,12-diaza-6,9-diazoniadispiro[5.2.5.3]heptadecane tetrabromide

Conditions	Yield
With triethylamine In methanol; water for 2h; Heating;	30%

2,4,6-trichloro-5-nitropyrimidine (4359-87-9) → Sodium salt of pyrimidinetetrasulfonic acid (107487-62-7)

Conditions	Yield
With sodium sulfite In 1,4-dioxane; water for 8h;	16%

Upstream product

• 106351-49-9 dilituric acid 
• 480-68-2 dilituric acid 
• 91-66-7 N,N-diethylaniline 
• 106351-49-9 5-nitrobarbituric acid 

Downstream Products

• 408352-74-9 2-chloro-5-nitropyrimidine-4,6-diamine 
• 99277-50-6 2,4-bis(benzyloxy)-6-chloro-5-nitropyrimidine 
• 1542549-24-5 ethyl 2-[(2,6-dichloro-5-nitropyrimidin-4-yl)oxy]benzoate 
• 1542549-21-2 ethyl 5-chloro-2-[(2,6-dichloro-5-nitropyrimidin-4-yl)amino]benzoate 
• 1228588-27-9 ethyl 2-((6-amino-2-chloro-5-nitropyrimidin-4-yl)(3-cyanobenzyl)amino)acetate 
• 1439393-86-8 tert-butyl 1-(4-(2,6-dichloro-5-nitropyrimidin-4-ylamino)phenyl)cyclobutylcarbamate 
• 1250867-75-4 3-(2,6-dichloro-5-nitropyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane 
• 83356-02-9 5-nitro-2,4,6-trimethoxypyrimidine 
• 91322-00-8 5-amino-2,4,6-trichloropyrimidine 

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