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4-Pyrimidinamine, 6-chloro-5-methyl- (9CI)

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4-Pyrimidinamine, 6-chloro-5-methyl- (9CI) manufacturers

4-Pyrimidinamine, 6-chloro-5-methyl- (9CI) Basic information
Product Name:4-Pyrimidinamine, 6-chloro-5-methyl- (9CI)
Synonyms:4-Pyrimidinamine, 6-Chloro-5-Methyl;6-AMINO-4-CHLORO-5-METHYLPYRIMIDINE;6-Chloro-5-methyl-pyrimidin-4-ylamine;4-Pyrimidinamine, 6-chloro-5-methyl- (9CI);6-chloro-5-methylpyrimidin-4-amine;6-Chloro-5-methyl-4-pyrimidinamine;4-Pyrimidinamine, 6-chloro-5-methyl- (9CI) ISO 9001:2015 REACH;4-Amino-6-chloro-5-methylpyrimidine
CAS:14394-56-0
MF:C5H6ClN3
MW:143.57
EINECS:
Product Categories:Heterocycle-Pyrimidine series;PYRIMIDINE
Mol File:14394-56-0.mol
4-Pyrimidinamine, 6-chloro-5-methyl- (9CI) Structure
4-Pyrimidinamine, 6-chloro-5-methyl- (9CI) Chemical Properties
Melting point 237-238℃
Boiling point 292.4±35.0 °C(Predicted)
density 1.349±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka2.41±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
HS Code 2933599590
MSDS Information
4-Pyrimidinamine, 6-chloro-5-methyl- (9CI) Usage And Synthesis
Synthesis
4,6-Dichloro-5-methylpyrimidine

4316-97-6

4-Pyrimidinamine, 6-chloro-5-methyl- (9CI)

14394-56-0

4,6-Dichloro-5-methylpyrimidine (Sigma-Aldrich No. 595446, 5 g, 30.70 mmol) was used as starting material and dissolved in a methanol solution of 7 M ammonia (15 ml, 105 mmol). The reaction mixture was placed in a sealed vial and the reaction was stirred at 140 °C for 40 min. After completion of the reaction, the resulting white suspension was poured into a mixture of water (300 ml) and ethyl acetate (600 ml), shaken well and left to stratify. The aqueous phase was separated and extracted with ethyl acetate (3 x 600 ml). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target compound 6-chloro-5-methyl-4-pyrimidinamine (3.10 g, 20.73 mmol, 68% yield) as a white solid. The product was analyzed by UPLC (retention time: 0.41 min) and the mass spectrum showed major peaks at m/z 144 ([M+H]+, 100%) and m/z 146 ([M+H]+, 33%), which was in accordance with the theoretical molecular weight of 143 (C5H6ClN3).1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.06 (s, 1H) , 7.09 (bs, 2H), 2.07 (s, 3H).

References[1] Patent: WO2009/3997, 2009, A1. Location in patent: Page/Page column 18
[2] Journal of the Chemical Society, 1947, p. 41,45
4-Pyrimidinamine, 6-chloro-5-methyl- (9CI) Preparation Products And Raw materials
Raw materials4,6-Dichloro-5-methylpyrimidine-->Ammonia-->Methanol
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