4-chloro-2-methanesulfonylpyrimidine
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With aq. NH3 In isopropyl alcohol | 100% |
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate at 180℃; under 150.015 - 900.09 Torr; for 2h; Neat (no solvent); | 95% |
With trichlorophosphate for 1.5h; Heating; | 52% |
Conditions | Yield |
---|---|
Stage #1: isocytosine With chlorosulfonic acid; trichlorophosphate at 20 - 95℃; Inert atmosphere; Stage #2: With ammonium hydroxide In water at 20℃; pH=~ 7; Cooling wit ice; | 92% |
Stage #1: isocytosine With trichlorophosphate for 1.5h; Reflux; Stage #2: With sodium carbonate In water pH=9; Cooling with ice; | 52% |
Conditions | Yield |
---|---|
With chlorosulfonic acid; trichlorophosphate at -5 - 90℃; for 5h; Inert atmosphere; | 73% |
2,6-Dichloropyrimidine
A
2-chloropyrimidin-4-amine
B
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 20℃; | A 69% B 23% |
With ammonium hydroxide at 20℃; for 5h; | A 59% B 37% |
With ammonium hydroxide In water at 20℃; for 5h; | A 59% B 37% |
Conditions | Yield |
---|---|
With ammonia; water | |
With ammonium hydroxide at 20℃; for 16h; |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With sulfuric acid; trichlorophosphate | |
With chlorosulphuric acid; trichlorophosphate |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With trichlorophosphate |
2,6-Dichloropyrimidine
ammonia
A
2-chloropyrimidin-4-amine
B
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
at 100℃; |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With ammonia | 51.3 g |
2-amino-4-chloropyrimidine
cyclopropanemethylamine
N4-(cyclopropylmethyl)pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
In ethanol at 100℃; for 16h; | 100% |
tert-butyl (1S)-2-(3-aminophenoxy)-1-(1H-indol-3-ylmethyl)ethylcarbamate
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
In ethanol | 98% |
In ethanol at 80℃; for 13h; | 98% |
(4-cyano-3-fluorophenyl)boronic acid
2-amino-4-chloropyrimidine
4-(2-amino-4-pyrimidinyl)-2-fluorobenzonitrile
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane; water at 95℃; for 3h; Suzuki Coupling; Inert atmosphere; | 97% |
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane; water at 95℃; for 3h; Suzuki coupling; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 4h; Reflux; | 95% |
With N-ethyl-N,N-diisopropylamine In acetonitrile for 4h; Reflux; | 95% |
With potassium carbonate In dimethyl sulfoxide at 100℃; for 0.333333h; Microwave irradiation; | 93% |
2-amino-4-chloropyrimidine
2-amino-4-iodopyrimidine
Conditions | Yield |
---|---|
With hydrogen iodide In water at 0 - 20℃; for 3h; | 95% |
With hydrogen iodide; sodium iodide In water at 20℃; for 3.5h; | 86% |
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 94% |
2-amino-4-chloropyrimidine
amino-4 hydroxy-2 toluene
5-(2-aminopyrimidin-4-ylamino)-2-methylphenol
Conditions | Yield |
---|---|
Stage #1: 2-amino-4-chloropyrimidine; amino-4 hydroxy-2 toluene With hydrogenchloride In ethanol; water at 90℃; for 18h; Stage #2: With potassium carbonate In ethanol; water; ethyl acetate Product distribution / selectivity; | 94% |
With hydrogenchloride In ethanol; water at 80 - 90℃; Product distribution / selectivity; |
2-amino-4-chloropyrimidine
6-bromo-5-methoxy-1H-indole
Conditions | Yield |
---|---|
Stage #1: 6-bromo-5-methoxy-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 15℃; for 0.5h; Stage #2: 2-amino-4-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 80℃; for 18h; | 94% |
(4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)methanol
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; | 93% |
2-amino-4-chloropyrimidine
m-nitrobenzene boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane at 95℃; Inert atmosphere; | 93% |
2-amino-4-chloropyrimidine
4-hydrazinylpyrimidin-2-amine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 80 - 100℃; Microwave irradiation; | 93% |
2-amino-4-chloropyrimidine
5-methoxy-4-aza-1H-indole
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; for 2h; | 92.13% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 92% |
With methanol | |
In methanol at 50℃; for 2.5h; |
4-chloro-2-methanesulfonylpyrimidine
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With aq. NH3 In isopropyl alcohol | 100% |
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate at 180℃; under 150.015 - 900.09 Torr; for 2h; Neat (no solvent); | 95% |
With trichlorophosphate for 1.5h; Heating; | 52% |
Conditions | Yield |
---|---|
Stage #1: isocytosine With chlorosulfonic acid; trichlorophosphate at 20 - 95℃; Inert atmosphere; Stage #2: With ammonium hydroxide In water at 20℃; pH=~ 7; Cooling wit ice; | 92% |
Stage #1: isocytosine With trichlorophosphate for 1.5h; Reflux; Stage #2: With sodium carbonate In water pH=9; Cooling with ice; | 52% |
Conditions | Yield |
---|---|
With chlorosulfonic acid; trichlorophosphate at -5 - 90℃; for 5h; Inert atmosphere; | 73% |
2,6-Dichloropyrimidine
A
2-chloropyrimidin-4-amine
B
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 20℃; | A 69% B 23% |
With ammonium hydroxide at 20℃; for 5h; | A 59% B 37% |
With ammonium hydroxide In water at 20℃; for 5h; | A 59% B 37% |
Conditions | Yield |
---|---|
With ammonia; water | |
With ammonium hydroxide at 20℃; for 16h; |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With sulfuric acid; trichlorophosphate | |
With chlorosulphuric acid; trichlorophosphate |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With trichlorophosphate |
2,6-Dichloropyrimidine
ammonia
A
2-chloropyrimidin-4-amine
B
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
at 100℃; |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With ammonia | 51.3 g |
2-amino-4-chloropyrimidine
cyclopropanemethylamine
N4-(cyclopropylmethyl)pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
In ethanol at 100℃; for 16h; | 100% |
tert-butyl (1S)-2-(3-aminophenoxy)-1-(1H-indol-3-ylmethyl)ethylcarbamate
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
In ethanol | 98% |
In ethanol at 80℃; for 13h; | 98% |
(4-cyano-3-fluorophenyl)boronic acid
2-amino-4-chloropyrimidine
4-(2-amino-4-pyrimidinyl)-2-fluorobenzonitrile
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane; water at 95℃; for 3h; Suzuki Coupling; Inert atmosphere; | 97% |
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane; water at 95℃; for 3h; Suzuki coupling; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 4h; Reflux; | 95% |
With N-ethyl-N,N-diisopropylamine In acetonitrile for 4h; Reflux; | 95% |
With potassium carbonate In dimethyl sulfoxide at 100℃; for 0.333333h; Microwave irradiation; | 93% |
2-amino-4-chloropyrimidine
2-amino-4-iodopyrimidine
Conditions | Yield |
---|---|
With hydrogen iodide In water at 0 - 20℃; for 3h; | 95% |
With hydrogen iodide; sodium iodide In water at 20℃; for 3.5h; | 86% |
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 94% |
2-amino-4-chloropyrimidine
amino-4 hydroxy-2 toluene
5-(2-aminopyrimidin-4-ylamino)-2-methylphenol
Conditions | Yield |
---|---|
Stage #1: 2-amino-4-chloropyrimidine; amino-4 hydroxy-2 toluene With hydrogenchloride In ethanol; water at 90℃; for 18h; Stage #2: With potassium carbonate In ethanol; water; ethyl acetate Product distribution / selectivity; | 94% |
With hydrogenchloride In ethanol; water at 80 - 90℃; Product distribution / selectivity; |
2-amino-4-chloropyrimidine
6-bromo-5-methoxy-1H-indole
Conditions | Yield |
---|---|
Stage #1: 6-bromo-5-methoxy-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 15℃; for 0.5h; Stage #2: 2-amino-4-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 80℃; for 18h; | 94% |
(4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)methanol
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; | 93% |
2-amino-4-chloropyrimidine
m-nitrobenzene boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane at 95℃; Inert atmosphere; | 93% |
2-amino-4-chloropyrimidine
4-hydrazinylpyrimidin-2-amine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 80 - 100℃; Microwave irradiation; | 93% |
2-amino-4-chloropyrimidine
5-methoxy-4-aza-1H-indole
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; for 2h; | 92.13% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 92% |
With methanol | |
In methanol at 50℃; for 2.5h; |
2-amino-4-chloropyrimidine
6-bromo-indoline
4-(6-bromoindolin-1-yl)pyrimidin-2-amine
Conditions | Yield |
---|---|
In 1,4-dioxane at 90℃; for 21h; | 92% |
With hydrogenchloride In water at 60℃; | 80% |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube; | 92% |
Conditions | Yield |
---|---|
In ethanol at 80℃; for 2.5h; | 91% |
2-amino-4-chloropyrimidine
(2-fluoro-pyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
With bis(di-tert-butylphenylphosphine)palladium(II) dichloride; potassium acetate In water; acetonitrile at 85℃; for 15h; Sealed tube; Inert atmosphere; | 91% |
pyrrolidine
2-amino-4-chloropyrimidine
4-(pyrrolidin-1-yl)pyrimidin-2-amine
Conditions | Yield |
---|---|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 20 - 120℃; Inert atmosphere; | 89.7% |
at 150℃; for 1h; Microwave irradiation; | 67% |
at 150℃; for 1h; Microwave irradiation; Sealed tube; | 67% |
1-indoline
2-amino-4-chloropyrimidine
isopropyl alcohol
2-amino-4-(indolin-1-yl)pyrimidine
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water | 89.6% |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 2h; Inert atmosphere; | 89.01% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 2h; Inert atmosphere; | 89.01% |
Conditions | Yield |
---|---|
In ethanol at 150℃; for 0.166667h; Microwave irradiation; Sealed tube; | 89% |
at 120℃; for 0.166667h; Microwave irradiation; | 54% |
6-bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]
2-amino-4-chloropyrimidine
4-(6-bromo-2',3',5',6'-tetrahydrospiro[indole-3,4'-pyran]-1(2H)-yl)pyrimidin-2-amine
Conditions | Yield |
---|---|
Stage #1: 6-bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]; 2-amino-4-chloropyrimidine With hydrogenchloride In water at 60℃; for 17.5h; Stage #2: With sodium hydroxide In water Cooling; | 88.3% |
2-[4-(4-amino-2-fluoro-phenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanol
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
Stage #1: 2-[4-(4-amino-2-fluoro-phenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanol; 2-amino-4-chloropyrimidine With hydrogenchloride In water Heating / reflux; Stage #2: With sodium hydroxide In water pH=10; | 88% |
2-amino-4-chloropyrimidine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In ethanol at 40℃; for 3h; Inert atmosphere; | 88% |
tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate
2-amino-4-chloropyrimidine
4-(1H-indol-3-yl)pyrimidin-2-amine
Conditions | Yield |
---|---|
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); caesium carbonate In water; isopropyl alcohol at 80℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 87% |
With caesium carbonate In methanol at 100℃; for 24h; Suzuki coupling; Inert atmosphere; | 73% |
2-amino-4-chloropyrimidine
2-Methoxyphenylboronic acid
4-(2-methoxyphenyl)pyrimidin-2-amine
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere; | 87% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 95℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere; | 86% |
2-amino-4-chloropyrimidine
2-amino-5-bromo-4-chloropyrimidine
Conditions | Yield |
---|---|
With bromine; acetic acid at 20℃; for 2h; | 86% |
With N-Bromosuccinimide In chloroform at 20℃; | 62% |
With N-Bromosuccinimide In methanol; acetonitrile at 20℃; for 0.5h; |
Empirical Formula: C4H4ClN3
Molecular Weight: 129.5477
Nominal Mass: 129 Da
Average Mass: 129.5477 Da
Monoisotopic Mass: 129.009375 Da
Index of Refraction: 1.617
Molar Refractivity: 31.56 cm3
Molar Volume: 90.1 cm3
Surface Tension: 66.4 dyne/cm
Density: 1.437 g/cm3
Flash Point: 144.1 °C
Enthalpy of Vaporization: 55.58 kJ/mol
Boiling Point: 314.6 °C at 760 mmHg
Vapour Pressure: 0.000461 mmHg at 25 °C
Melting Point: 155-160 °C (dec.)
Appearance: White solid
Structure of 2-Amino-4-chloropyrimidine (CAS NO.3993-78-0):
IUPAC Name: 4-Chloropyrimidin-2-amine
Canonical SMILES: C1=CN=C(N=C1Cl)N
InChI: InChI=1S/C4H4ClN3/c5-3-1-2-7-4(6)8-3/h1-2H,(H2,6,7,8)
InChIKey: DBGFGNCFYUNXLD-UHFFFAOYSA-N
Product Category of 2-Amino-4-chloropyrimidine (CAS NO.3993-78-0): APIs & Intermediate;Pyridines, Pyrimidines, Purines and Pteredines;Amines;Bases & Related Reagents;Heterocycles;Nucleotides;Pyrazines, Pyrimidines & Pyridazines;Halogenated Heterocycles;Heterocyclic Building Blocks
2-Amino-4-chloropyrimidine (CAS NO.3993-78-0) is usually used for the synthesis of pesticides such as Chlorimuron-ethyl.
The Hazard Codes: Xi,Xn
The Risk Statements:
22: Harmful if swallowed
41: Risk of serious damage to eyes
36/37/38: Irritating to eyes, respiratory system and skin
37/38: Irritating to respiratory system and skin
The Safety Statements information:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
36/39: Wear suitable protective clothing and eye/face protection
Hazard Note: Irritant
2-Amino-4-chloropyrimidine , its cas register number is 3993-78-0. It also can be called (4-Chloropyrimidin-2-yl)amine ; 4-Chloro-2-pyrimidinamine ; and 2-Pyrimidinamine,4-chloro- .
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