4-Chloro-2-methylthiopyrimidine synthesis
- Product Name:4-Chloro-2-methylthiopyrimidine
- CAS Number:49844-90-8
- Molecular formula:C5H5ClN2S
- Molecular Weight:160.62
4-Chloro-2-methylthiopyrimidine can be produced from 2-thiouracil as raw material, dimethyl sulfate as methylation reagent, and thionyl chloride and phosphorus oxychloride as chlorination reagents by methylation and chlorination reaction.
5751-20-2
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$14.00/1g
49844-90-8
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$5.00/1g
Yield:49844-90-8 87.6%
Reaction Conditions:
with thionyl chloride in dichloromethane;N,N-dimethyl-formamide at 40; for 3 h;
Steps:
4-Chloro-2-(methylthio)pyrimidine (15)
To a solution of 2-methylthio-4-ketopyrimidine (14,10.27 g, 70.4 mmol) in DCM (20 mL) and DMF (10 mL)mixed solution, thionyl chloride (3.05 mL, 42.2 mmol) solution was slowly added dropwise while heating. After addition, the reaction mixture was stirred at 40 °C for 3 h. After quenching with saturated NaHCO3, the solution was adjusted to a neutral pH and the solution was extracted three times with DCM. The organic phases were washed with saturated NaHCO3 solution and saturated NaCl solution and dried over anhydrous Na2SO4. After filtering to remove the anhydrous Na2SO4, the solution was distilled at40 °C to remove solvents under atmospheric pressure to give product 15 as a yellow oil (10.19 g, 87.6%). 1H NMR(300 MHz, CDCl3) δ 8.38 (d, J = 5.2 Hz, 1H), 6.99 (d,J = 5.2 Hz, 1H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ174.0, 161.0, 158.0, 116.4, 14.3; HRMS ([M + H]+): m/zcalcd for C5H5ClN2S: 160.9940; found: 160.99335.
References:
Li, Shuting;Yang, Wanfeng;Ji, Min;Cai, Jin;Chen, Junqing [Journal of Chemical Research,2019,vol. 43,# 1-2,p. 14 - 19]
5751-20-2
309 suppliers
$14.00/1g
49844-90-8
252 suppliers
$5.00/1g
5751-20-2
309 suppliers
$14.00/1g
49844-90-8
252 suppliers
$5.00/1g