ChemicalBook CAS DataBase List 2-Chloro-4-methylpyrimidine

2-Chloro-4-methylpyrimidine synthesis

13synthesis methods

Product Name:2-Chloro-4-methylpyrimidine
CAS Number:13036-57-2
Molecular formula:C5H5ClN2
Molecular Weight:128.56

5424-21-5

13036-57-2

Step A: Synthesis of 2-chloro-4-methylpyrimidine To a vigorously stirred slurry containing 50.0 g (0.31 mol) of 2,6-dichloro-4-methylpyrimidine, 250 mL of ethanol (EtOH), and 250 mL of water, 41 g (0.63 mol) of zinc powder and 0.78 g (3.08 mmol) of iodine were sequentially added. The reaction mixture was heated to reflux at 70°C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to remove ethanol and subsequently extracted with dichloromethane (DCM). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to remove solvent. The residue was purified by silica gel column chromatography using a hexane/DCM solvent mixture as eluent, resulting in 20.6 g (53% yield) of 2-chloro-4-methylpyrimidine as a white solid. The structure of the product was confirmed by 1H-NMR (d6-DMSO, 400 MHz) δ 8.59 (d, 1H, J=4.9 Hz), 7.44 (d, 1H, J=4.9 Hz), and 3.29 (s, 3H), and ESIMS: 129.11 (M+H+).

5424-21-5 Synthesis

5424-21-5
332 suppliers
$10.00/5g

13036-57-2
335 suppliers
$6.00/1g

Yield:13036-57-2 74.4%

Reaction Conditions:

with ammonium hydroxide;zinc for 2 h;Reflux;

Steps:

1.3 (3) Synthesis of 2-chloro-4-methyl pyrimidine
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 74.4%

References:

Shenyang Pesticide Chemical Co., Ltd.;Li, Bin;Wang, Gang;Fan, Xiaoxi;Lu, Liang;Li, Keke;Shi, Xuegeng CN105732587, 2016, A Location in patent:Paragraph 0117; 0118; 0119

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3934-20-1 Synthesis