Phosphorus oxychloride → 4-Chloro-7-methylthieno(3,2-d)pyrimidine

反応式

[CH3:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[S:4][CH:3]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:10]1[C:5]2[S:4][CH:3]=[C:2]([CH3:1])[C:6]=2[N:7]=[CH:8][N:9]=1

参加物

反応物 3

HCID 24813Phosphorus oxychloride

HCID 516892Sodium Bicarbonate

HCID 1354396367-methyl-3H,4H-thieno[3,2-d]pyrimidin-4-one

生成物 1

HCID 27775864-Chloro-7-methylthieno(3,2-d)pyrimidine収率 96%

実験手順

A solution of 7-methyl-3H-thieno[3,2-d]pyrimid-4-one (3, 2.9 g, 18 mmol) in phosphorus oxychloride (18 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature and then poured into a saturated aqueous solution of sodium bicarbonate to neutralize. The aqueous mixture was extracted with diethyl ether. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 4-chloro-7-methylthieno[3,2-d]pyrimidine (3.1 g, 96% yield) as a white solid.