2-Chloro-4-methylpyrimidine
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2-Chloro-4-methylpyrimidine
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CAS No:
13036-57-2
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Formula:
C5H5ClN2
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Chemical Name:
2-Chloro-4-methylpyrimidine
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Synonyms:
2-CHLORO-4-METHYLPYRIMIDINE;Pyrimidine, 2-chloro-4-methyl- (6CI,7CI,8CI,9CI);2-CHLORO-4-METHYLPYRIMIDINE 98%;2-Chloro-6-methylpyrimidine;2-Chloro-4-methyl-1,3-diazine;chloro-4-MethylpyriMidine
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CAS No:
Characteristics
25.8
1.6
pale yellow solid
1.234±0.06 g/cm3(Predicted)
35-36°C
94°C/17mmHg(lit.)
98℃
1.530
keep cold/store under nitrogen
0.209mmHg at 25°C
Safety Information
IRRITANT
NONH for all modes of transport
3
22-41-37/38
26-39
Xi,Xn
Irritant
Toxic
P261-P280-P305 + P351 + P338
H302-H315-H318-H335
2-Chloro-4-methylpyrimidine Use and Manufacturing
To the reaction flask were sequentially added 2, 4-dichloro-6-methyl-pyrimidine (15.00 g, 92.00 mmol), zinc powder (18.05 g, 276.00 mmol), ammonia (38.70 g, 276 mmol) and stirred at to the reaction flask was added water (120 ml). The reaction was heated at reflux for 2 hours, the reaction solution was cooled to room temperature, suction filtered, the filtrate was extracted with ethyl acetate (2x200 ml), the organic layer was post-saturated brine (150 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure the residue was purified by column chromatography (eluent to PE: EA = 5: 1), to give a white solid 8.8 g, yield 74.4percentStep A: 2-Chloro-4-methylpyrimidine; CH, Q Example 1.1.26: (4-methylpyrimidin-2-yl)methanamine; MeMgCl (3M solution in THF, 4.47 mL, 13.42 mmol) was added dropwise to a stirred solution of the 2, 4-dichloropyrimidine (2 g, 13.42 mmol) and Fe(acac)To a finely dispersed suspension of 2-chloropyrimidine (8.01 g, 69.9 mmol) in a 10: 1 mixture of [ET2O-THF] (500 mL) [AT-30°C] was added dropwise MeLi (46 mL, 1.6M in [ET20, ] 73.6 mmol). The reaction mixture was stirred [AT-30°C] for 30 min, and was then warmed to [0°C] and stirred for 30 min. To the reaction mixture was then added a 1: 1: 20 mixture of H2O- [HOAC-THF] (100 mL), and the mixture was stirred at [0°C] for 10 min. To the mixture was then added a solution of DDQ (16.7 g, 73.6 mmol) in THF (100 [ML), ] and the mixture was stirred and warmed to room temperature for 30 min. The mixture was then diluted with [ET2O] (300 mL) and washed with IN aq. [NAOH] [(3X100] [ML)] followed by brine (300 mL). The organic phase was then dried over anhydrous [MGSO4, ] filtered, concentrated in vacuo, and purified by flash chromatography using EtOAc-hexanes (1: 2) as eluent to afford 6.06 g of 2-chloro-4- methylpyrimidine (67percent) as white crystalline plates. To a solution of 2-chloro-4-methylpyrimidine (6.06 g, 47.1 mmol) in [MEOH] (40 [ML)] was added hydrazine monohydrate (10 mL, 206 [MMOL).] The solution was stirred for 16 h at room temperature and then purified by reverse phase HPLC to provide 4.43 g of the title compound [(76percent)] as a white solid. MH+ 125.2-Chloro-4-methyl-pyrimidine (51):
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