5734-64-5

Basic information

• Product Name: 2-Amino-4-chloro-6-methoxypyrimidine
• Synonyms: 2-AMINO-4-CHLORO-6-METHOXYPYRIMIDINE;2-AMINO-4-METHOXY-6-CHLORO PYRIMIDINE;2-AMINO-6-CHLORO-4-METHOXYPYRIMIDINE;4-Chloro-6-methoxy-2-pyrimidinamine;4-CHLORO-6-METHOXY-2-PYRIMIDINYLAMINE;4-CHLORO-6-METHOXY-PYRIMIDIN-2-AMINE;4-CHLORO-6-METHOXY-PYRIMIDIN-2-YLAMINE;ACMP
• CAS NO: 5734-64-5
• Molecular Formula: C₅H₆ClN₃O
• Molecular Weight: 159.57
• EINECS: 410-050-9
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Pyrimidine;Pyrimidines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrimidinesHeterocyclic Building Blocks;Heterocycle-Pyrimidine series
• Mol File: 5734-64-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 168-171 °C(lit.)
• Boiling Point: 349.357 °C at 760 mmHg
• Flash Point: 165.086 °C
• Appearance: Light yellow/Crystalline Powder
• Density: 1.6625 (rough estimate)
• Vapor Pressure: 4.73E-05mmHg at 25°C
• Refractive Index: 1.4510 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.96±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4-chloro-6-methoxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-chloro-6-methoxypyrimidine(5734-64-5)
• EPA Substance Registry System: 2-Amino-4-chloro-6-methoxypyrimidine(5734-64-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-2
• WGK Germany: 1
• RTECS: UV6260335
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 5734-64-5(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline powder

Uses

2-Amino-4-chloro-6-methoxy-pyrimidine is one of the two major metabolites formed in the degradation of chlorimuron-ethyl; a pre- and post-emergence herbicide for the control of important broad-leaved weeds in soybean and maize.

InChI:InChI=1/C5H6ClN3O/c1-10-4-2-3(6)8-5(7)9-4/h2H,1H3,(H2,7,8,9)

Synthetic route

methanol (67-56-1) + 2-Amino-4,6-dichloropyrimidine (56-05-3) + sodium methylate (124-41-4) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
at 17℃; for 4.5h; Product distribution / selectivity; Heating / reflux;	97%
for 20h; Heating / reflux;	90%

2-Amino-4,6-dichloropyrimidine (56-05-3) + sodium methylate (124-41-4) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
In acetone at 17 - 30℃; for 6.5h; Product distribution / selectivity;	95.3%
In acetic acid methyl ester at 17 - 30℃; for 6.5h; Product distribution / selectivity;	94.6%
In methanol for 20h; Heating / reflux;	90%

methanol (67-56-1) + 2-Amino-4,6-dichloropyrimidine (56-05-3) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
With potassium carbonate at 20℃; for 2h; Product distribution / selectivity; Heating / reflux;	95%
With sodium methylate In methanol for 20h; Reflux;	90%
Stage #1: methanol With sodium hydride In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: 2-Amino-4,6-dichloropyrimidine In tetrahydrofuran for 15h; Inert atmosphere;	84%

2,4-dichloro-6-methoxypyrimidine (43212-41-5) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
With ethanol; ammonia at 100℃;

2-amino-6-methoxy-3H-pyrimidin-4-one → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
With trichlorophosphate

2,4-dichloro-6-methoxypyrimidine (43212-41-5) + ammonia (7664-41-7) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
at 100℃; im Rohr;

chlorimuron ethyl (90982-32-4) → 4-methoxypyrimidin-2-amine (155-90-8) + 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + ethyl 2-(aminosulfonyl)benzoate (59777-72-9) + saccharin (81-07-2) + N-(6-Chloro-4-methoxypyrimidin-2-yl)urea + chlorimuron + benzoic acid, ethyl benzoate

Conditions	Yield
With water for 2h; Product distribution; Rate constant; Irradiation; var. pH values;

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + N-methylaniline (100-61-8) → 2-amino-6-(N-methylanilino)pyrimidin-4(3H)-one (25706-78-9)

Conditions	Yield
at 289.84 - 299.84℃; for 0.0666667h;	97%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C14H9NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(phenoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C14H9NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	97%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) → 4-methoxypyrimidin-2-amine (155-90-8)

Conditions	Yield
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	94%
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	90%
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	90%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + <(4-nitrophenyl)oxy>sulfonyl isocyanate (73748-48-8) → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((4-nitrophenoxy) sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; <(4-nitrophenyl)oxy>sulfonyl isocyanate In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	94%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C10H9NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(ethoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C10H9NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	92%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 4-chlorobenzaldehyde (104-88-1) + diethyl malonate (105-53-3) → (S)-diethyl 2-(((4-chloro-6-methoxypyrimidin-2-yl)amino)(4-methoxyphenyl)methyl)malonate

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)((1S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In para-xylene at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	90%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C11H11NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(isopropoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C11H11NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	90%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C11H11NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(propoxycarbonyl) phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C11H11NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	89%

fur-2-ylboronic acid (13331-23-2) + 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) → 4-(furan-2-yl)-6-methoxypyrimidin-2-amine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 3h; Inert atmosphere;	87.29%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate (17823-58-4) → (E)-3-(4-Chloro-6-methoxy-pyrimidin-2-ylamino)-2-cyano-3-methylsulfanyl-acrylic acid ethyl ester

Conditions	Yield
With sodium hydride In N,N-dimethyl acetamide; toluene Ambient temperature;	85%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + Tetraethylene glycol (112-60-7) → 2-(2-(2-(2-(2-amino-6-methoxypyrimidin-4-yloxy)ethoxy)ethoxy)ethoxy)ethanol (1268273-35-3)

Conditions	Yield
Stage #1: Tetraethylene glycol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Reflux; Inert atmosphere; Stage #2: 2-amino-4-chloro-6-methoxypyrimidine In N,N-dimethyl-formamide at 80℃; for 3h;	83%
Stage #1: Tetraethylene glycol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-amino-4-chloro-6-methoxypyrimidine In N,N-dimethyl-formamide; mineral oil at 80℃; for 3h; Inert atmosphere;	83%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-hydroxyphenyl 2-chloroethyl ether (4792-79-4) → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(2-chloroethoxy) phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; 2-hydroxyphenyl 2-chloroethyl ether In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	83%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C10H6F3NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-((2,2,2-trifluoroethoxy)carbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C10H6F3NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	83%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + N-butylamine (109-73-9) → N4-butyl-6-methoxypyrimidine-2,4-diamine

Conditions	Yield
With triethylamine In methanol at 70℃; for 12h;	82%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + benzyl alcohol (100-51-6) → 4-(benzyloxy)-6-methoxypyrimidin-2-amine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 3h; Solvent; Temperature; Inert atmosphere;	81.6%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 5-(4-Nitro-phenyl)-furan-2-carbonyl isothiocyanate (140160-21-0) → 1-(4-chloro-6-methoxy-pyrimidin-2-yl)-3-[5-(4-nitro-phenyl)-furan-2-carbonyl]-thiourea

Conditions	Yield
sonication;	81%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 5-(2-chlorophenyl)-2-furoylisothiocyanate (304437-60-3) → 1-(4-chloro-6-methoxy-pyrimidin-2-yl)-3-[5-(2-chloro-phenyl)-furan-2-carbonyl]-thiourea

Conditions	Yield
sonication;	81%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C9H7NO6S (73748-49-9) → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(methoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C9H7NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	81%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 4-Methoxybenzyl alcohol (105-13-5) → 4-methoxy-6-((4-methoxybenzyl)oxy)pyrimidin-2-amine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;	79.6%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 3-Isocyanatosulfonyl-1-methyl-1H-indole-2-carboxylic acid methyl ester → C17H16ClN5O6S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In benzene for 4h; Heating;	79%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-iodoethyl 2-hydroxybenzoate → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-((2-iodoethoxy)carbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; 2-iodoethyl 2-hydroxybenzoate In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	79%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-tri-n-butylstannylpyridine (17997-47-6) → 4-methoxy-6-(pyridin-2-yl)pyrimidin-2-amine

Conditions	Yield
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 120℃; for 3h; Inert atmosphere;	78.91%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C9H8INO5S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(2-iodoethoxy) phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C9H8INO5S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	78%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-fluoro-6-isocyanatosulfonyl-benzoic acid methyl ester → C14H12ClFN4O6S

Conditions	Yield
	75%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C7H4N2O6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-nitrophenoxy) sulfonyl) amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C7H4N2O6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	75%

formaldehyd (50-00-0) + 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 5-(4-fluorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione (41421-13-0) → 3-((4-chloro-6-methoxypyrimidin-2-ylamino)methyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole-2(3H)-thione

Conditions	Yield
In ethanol for 3h; Reflux;	74.5%

Upstream product

• 67-56-1 methanol 
• 56-05-3 2-Amino-4,6-dichloropyrimidine 
• 124-41-4 sodium methylate 
• 43212-41-5 2,4-dichloro-6-methoxypyrimidine 
• 7664-41-7 ammonia 
• 90982-32-4 chlorimuron ethyl 

Downstream Products

• 98525-48-5 2-amino-6-(diethylamino)-4-methoxypyrimidine 
• 155-90-8 4-methoxypyrimidin-2-amine 
• 1194-21-4 6-chloroisocytosine 
• 25706-78-9 2-amino-6-(N-methylanilino)pyrimidin-4(3H)-one 
• 896448-88-7 C₁₅H₁₃Cl₃N₄O₃S 
• 13012-26-5 4-chloro-6-methoxy-N,N-dimethylpyrimidin-2-amine 
• 944401-63-2 4-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-pyrimidin-2-ylamine 
• 36082-45-8 5-bromo-4-methoxypyrimidine-2-ylamine 
• 1374830-75-7 C₁₈H₁₃ClF₃N₅O₃S 
• 1416567-35-5 C₁₅H₁₄BrClN₄O₆S 

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