39906-04-2

Basic information

• Product Name: 5-Amino-4,6-dichloro-2-methylpyrimidine
• Synonyms: 5-AMINO-4,6-DICHLORO-2-METHYLPYRIMIDINE;4,6-DICHLORO-2-METHYLPYRIMIDIN-5-AMINE;2-METHYL-4,6-DICHLORO-5-AMINOPYRIMIDINE;TIMTEC-BB SBB003764;4,6-DICHLORO-2-METHYL-PYRIMIDIN-5-YLAMINE;2-Methyl-4,6-dichloro-5-aminop;2-methyl-4,6-dichloro-5-aminopyrimidine (intermediate of moxonidine hcl);5-Amino-4,6-Dichloro-2-Methylpytimidine
• CAS NO: 39906-04-2
• Molecular Formula: C₅H₅Cl₂N₃
• Molecular Weight: 178.0193
• EINECS: 419-110-9
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Pyrimidine;(intermediate of moxonidine hcl);(intermediate of moxonidine)
• Mol File: 39906-04-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 70-73 °C(lit.)
• Boiling Point: 257.7 °C at 760 mmHg
• Flash Point: 109.6 °C
• Appearance: /
• Density: 1.504 g/cm³
• Vapor Pressure: 0.0143mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -2.55±0.39(Predicted)
• CAS DataBase Reference: 5-Amino-4,6-dichloro-2-methylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-4,6-dichloro-2-methylpyrimidine(39906-04-2)
• EPA Substance Registry System: 5-Amino-4,6-dichloro-2-methylpyrimidine(39906-04-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 39906-04-2(Hazardous Substances Data)

Usage

Appearance

White to Yellow to Green powder to crystal

Uses

5-Amino-4,6-dichloro-2-methylpyrimidine is a useful research chemical for organic synthesis and other chemical and pharmacological processes.

InChI:InChI=1/C5H5Cl2N3/c1-2-9-4(6)3(8)5(7)10-2/h8H2,1H3

Synthetic route

4,6-dichloro-2-methyl-5-nitropyrimidine (13162-43-1) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 4h;	84%
With iron In methanol; acetic acid at 60℃; for 2h;	83%
With hydrogenchloride; iron In methanol; water at 75℃; for 5h;	67.8%

5-amino-4,6-dihydroxy-2-methylpyrimidine (98797-08-1) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
With trichlorophosphate at 110℃; for 20h; Inert atmosphere; Sealed tube;	26%
With trichlorophosphate at 110℃; for 20h; Sealed tube; Inert atmosphere;	26%

5-amino-6-chloro-2-methyl-3H-pyrimidin-4-one (98025-13-9) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
With N,N-diethylaniline; trichlorophosphate

2-methyl-5-nitro-1H-pyrimidine-4,6-dione (680881-02-1) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-diethyl-aniline; POCl3 2: aqueous Fe(OH)2 View Scheme

2-methyl-1H-pyrimidine-4,6-dione (40497-30-1) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; HNO3 2: N,N-diethyl-aniline; POCl3 3: aqueous Fe(OH)2 View Scheme

4,6-dichloro-2-methyl-5-nitropyrimidine (13162-43-1) + iron (7439-89-6) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
With acetic acid In methanol
With acetic acid In methanol

N-(4,6-dihydroxy-2-methylpyrimidin-5-yl)acetamide (98797-16-1) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water; methanol / 15.5 h / 20 - 50 °C / Inert atmosphere 2: trichlorophosphate / 20 h / 110 °C / Inert atmosphere; Sealed tube View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / methanol / 15.5 h / Inert atmosphere; Heating 2: trichlorophosphate / 20 h / 110 °C / Sealed tube; Inert atmosphere View Scheme

C5H5N3O4 → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / Reflux 2: acetic acid; iron / methanol / 60 °C View Scheme

6-hydroxy-2-methyl-5,6-dihydropyrimidin-4(3H)-one (1194-22-5) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid; trifluoroacetic acid / water / 20 °C 2: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / Reflux 3: acetic acid; iron / methanol / 60 °C View Scheme

2-methyl-4,6-dihydroxypyrimidine (1194-22-5) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid; acetic acid / 2 h / 0 °C 2: trichlorophosphate; N,N-diethylaniline / 3 h / 115 °C 3: iron; hydrogenchloride / methanol; water / 5 h / 75 °C View Scheme
Multi-step reaction with 3 steps 1: nitric acid / 2 h / 20 °C 2: trichlorophosphate / N,N-dimethyl-aniline / 2.5 h / Heating / reflux 3: iron / methanol; acetic acid / 2 h / 60 - 65 °C View Scheme

2-methyl-4,6-dihydroxy-5-nitropyrimidine (53925-27-2) → 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate; N,N-diethylaniline / 3 h / 115 °C 2: iron; hydrogenchloride / methanol; water / 5 h / 75 °C View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / N,N-dimethyl-aniline / 2.5 h / Heating / reflux 2: iron / methanol; acetic acid / 2 h / 60 - 65 °C View Scheme

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + cyclohexylamine (108-91-8) → 6-chloro-N4-cyclohexyl-2-methylpyrimidine-4,5-diamine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 120℃;	100%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + methyl iodide (74-88-4) → 4,6-dichloro-N,2-dimethylpyrimidin-5-amine

Conditions	Yield
	100%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + m-dimethylaminoaniline (2836-04-6) → 6-chloro-N4-[3'-(N',N'-dimethylamino)phenyl]-2-methylpyrimidine-4,5-diamine (1362239-25-5)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; for 0.166667h; Sealed vial; Microwave irradiation;	98%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 2-methoxy-phenylamine (90-04-0) → 6-chloro-N4-(2′-methoxyphenyl)-2-methylpyrimidine-4,5-diamine (1609009-25-7)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	98%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	98%

3-aminobenzoic acid ethyl ester (582-33-2) + 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) → ethyl 3-((5-amino-6-chloro-2-methylpyrimidin-4-yl)amino)benzoate (1609009-33-7)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	98%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	98%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 3-chloro-4-fluorophenylamine (367-21-5) → 6-chloro-N4-(3-chloro-4-fluorophenyl)-2-methylpyrimidine-4,5-diamine

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 16h; Reflux;	98%

methanol (67-56-1) + 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) → 5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine (88474-31-1)

Conditions	Yield
With sodium methylate for 12h; Ambient temperature;	97%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) → 6-chloro-2-methylpyrimidine -4,5-diamine (933-80-2)

Conditions	Yield
With ammonium hydroxide In dichloromethane at 120℃; Sealed tube;	96%
With ammonia In isopropyl alcohol at 150℃; for 16h; Sealed tube;	91%
With ammonia In water at 70 - 100℃;	63%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 2,4-difluorophenylamine (367-25-9) → 6-chloro-N4-(2,4-difluorophenyl)-2-methylpyrimidine-4,5-diamine

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 16h; Reflux;	96%

4-aminotetrahydropyran (38041-19-9) + 5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) → 6-chloro-2-methyl-N4-(tetrahydro-2H-pyran-4-yl)-pyrimidine-4,5-diamine (1231220-81-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 100℃; for 48h; Autoclave; Large scale;	95.9%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 150℃; for 16h; In a sealed tube;
With ammonia; N-ethyl-N,N-diisopropylamine In water; isopropyl alcohol at 150℃; for 4h; Sealed tube;

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + methylamine (74-89-5) → 6-chloro-N4,2-dimethyl-pyrimidine-4,5-diamine

Conditions	Yield
In 1,4-dioxane; water at 80℃; Sealed tube;	95%
With N-ethyl-N,N-diisopropylamine In water; isopropyl alcohol at 150℃; for 4h; Sealed tube;	77%
With ethanol at 120℃;
In isopropyl alcohol Heating;

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) → 4-chloro-5-cyano-1,2,3-triazole (88474-32-2)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water 1.)-5 deg C, 1.5 h 2.)20 deg C, 1.5 h;	95%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + sodium methylate (124-41-4) → 5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine (88474-31-1)

Conditions	Yield
In methanol at 20℃;	95%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + m-Anisidine (536-90-3) → 6-chloro-N4-(3’-methoxyphenyl)-2-methylpyrimidine-4,5-diamine (1609009-26-8)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	95%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	95%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + p-toluidine (106-49-0) → 6-chloro-2-methyl-N4-(4-methylphenyl)pyrimidine-4,5-diamine (592520-19-9)

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 16h; Reflux;	93%
With hydrogenchloride In ethanol; water at 20℃; for 8h; Reflux;
With hydrogenchloride In ethanol; water at 82℃; for 24h;

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 3-chloro-aniline (108-42-9) → 6-chloro-N4-(3’-chlorophenyl)-2-methylpyrimidine-4,5-diamine (1609009-27-9)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	93%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	93%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 4-trifluoromethylphenylamine (455-14-1) → 6-chloro-2-methyl-N4-(4-(trifluoromethyl)phenyl)pyrimidine-4,5-diamine

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 16h; Reflux;	93%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 1,3,5-trimethyl-benzene (108-67-8) → 4,6-dichloro-N-mesityl-2-methylpyrimidin-5-amine

Conditions	Yield
With I,I-bis(acetoxy)iodobenzene at 20℃; regioselective reaction;	93%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + m-cyanoaniline (2237-30-1) → 3-((5-amino-6-chloro-2-methylpyrimidin-4-yl)amino)benzonitrile (1609009-30-4)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	91%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	91%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + o-chlorobenzoyl chloride (609-65-4) → 2-chloro-N-(4,6-dichloro-2-methylpyrimidin-5-yl)benzamide (1418274-03-9)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 70 - 75℃; for 5h; Inert atmosphere;	90.7%
In 1-methyl-pyrrolidin-2-one at 80℃; for 5h;
In N,N-dimethyl acetamide at 0℃;

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate (130418-90-5, 130495-08-8) → C16H21ClN4O2 (1208231-44-0)

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 80℃; for 2h;	90%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 3-amino benzophenone (2835-78-1) → 6-chloro-N4-(3’-benzoylphenyl)-2-methylpyrimidine-4,5-diamine (1609009-28-0)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	89%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	89%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + benzo[1,3]dioxolo-5-ylamine (14268-66-7) → 6-chloro-N4-[3,4-methylenedioxyphenyl]-2-methylpyrimidine-4,5-diamine (1609009-32-6)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	89%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	89%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 4-methoxy-aniline (104-94-9) → 6-chloro-4-N-(4-methoxyphenyl)-2-methylpyrimidine-4,5-diamine hydrochloride (1198109-46-4)

Conditions	Yield
Stage #1: 5-amino-4,6-dichloro-2-methylpyrimidine; 4-methoxy-aniline In ethanol Stage #2: With hydrogenchloride In ethanol at 49 - 80℃;	88%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + Benzoyl isothiocyanate (532-55-8) → N-(7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-yl)benzamide

Conditions	Yield
In acetone for 3h; Reflux;	87%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + N-(4-fluorophenyl)-N'-(4-hydroxyphenyl)cyclopropane-1,1-dicarboxamide (849217-60-3) → N-(4-((5-amino-6-chloro-2-methylpyrimidin-4-yl)oxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	87%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 2-formylthiophene-3-boronic acid (4347-31-3) → C10H6ClN3S

Conditions	Yield
With sodium hydroxide In ethanol at 75℃; for 0.5h; Suzuki-Miyaura Coupling; Microwave irradiation; Green chemistry;	85%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + 4-propoxyaniline (4469-80-1) → 6-chloro-2-methyl-N4-(4’-propoxyphenyl)pyrimidine-4,5-diamine (1609009-31-5)

Conditions	Yield
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation;	84%
With hydrogenchloride In 2-methyl-propan-1-ol; water at 150℃; Microwave irradiation; Sealed tube;	84%

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + aniline (62-53-3) → 6-chloro-2-methyl-N4-phenylpyrimidine-4,5-diamine (129006-34-4)

Conditions	Yield
With hydrogenchloride In ethanol; water at 82℃; for 24h;	83.1%
With hydrogenchloride In ethanol; water at 20℃; for 16h; Reflux;	81%
With hydrogenchloride In ethanol; water for 1h; Heating;
With hydrogenchloride In ethanol; water for 3h; Heating;	12 g

Upstream product

• 53925-27-2 2-methyl-4,6-dihydroxy-5-nitropyrimidine 
• 1194-22-5 2-methyl-4,6-dihydroxypyrimidine 
• 1194-22-5 6-hydroxy-2-methyl-5,6-dihydropyrimidin-4(3H)-one 
• 98797-08-1 5-amino-4,6-dihydroxy-2-methylpyrimidine 
• 98797-16-1 N-(4,6-dihydroxy-2-methylpyrimidin-5-yl)acetamide 
• 13162-43-1 4,6-dichloro-2-methyl-5-nitropyrimidine 
• 7439-89-6 iron 
• 40497-30-1 2-methyl-1H-pyrimidine-4,6-dione 
• 680881-02-1 2-methyl-5-nitro-1H-pyrimidine-4,6-dione 
• 98025-13-9 5-amino-6-chloro-2-methyl-3H-pyrimidin-4-one 

Downstream Products

• 169883-27-6 4-N-<2-bromo-4-(1-methylethyl)phenyl>-6-chloro-2-methylpyrimidine-4,5-diamine 
• 1026753-49-0 6-chloro-N⁴-(2-chloro-4,6-dimethoxy-phenyl)-2-methyl-pyrimidine-4,5-diamine 
• 75438-54-9 4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine 
• 1187205-76-0 4-chloro-6-(4-methoxyphenyl)-2-methyl-pyrimidin-5-ylamine 
• 1187205-74-8 4-chloro-6-(2-fluoro-4-trifluoromethylphenyl)-2-methylpyrimidin-5-ylamine 
• 140421-32-5 2-methyl-9-phenyl-9H-purine 
• 129006-35-5 6-chloro-2-methyl-9-phenyl-9H-purine 

Relevant articles and documents

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PROCESS FOR THE PREPARATION OF AN INTERMEDIATE FOR A TRIAZOLOPYRIMIDINE CARBONUCLEOSIDE

A process for the preparation of 4,6-dihalopyrimidin-5-amines of formula (II), or salts thereof, which comprises reacting 5-aminopyrimidin-4,6-diols of formula (III), or salts thereof, or a solvate either of the compound of formula (III) or of a salt thereof, with a halogenating agent, new intermediates useful in the preparation of the compound of formula (II) and processes for the preparation of these intermediates. The invention also refers to a process for the preparation of ticagrelor or a pharmaceutically acceptable salt thereof from 4,6-dihalo-2-(propylthio)pyrimidin-5-amine of formula (IIA).