Dimethylformamide → 4,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

反応式

P(Cl)(Cl)([Cl:3])=O.CN([CH:9]=[O:10])C.O[C:12]1[NH:17][C:16]([S:18][CH3:19])=[N:15]C(=O)C=1.Cl[CH:22]=[C:23]([Cl:25])Cl>>[Cl:25][C:23]1[C:22]([CH:9]=[O:10])=[C:12]([Cl:3])[N:17]=[C:16]([S:18][CH3:19])[N:15]=1

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 6575Trichloroethylene

HCID 24813Phosphorus oxychloride

HCID 178503560HCID 178503560、化合物

生成物 1

HCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde収率 61%

反応条件

温度: 80 °C

実験手順

To the solution of phosphorus oxychloride (65 mL, 0.70 mol) in trichloroethylene (46.5 mL) was added DMF (25 mL, 0.32 mol) slowly to keep the temperature between 5° C. to 10° C. The solution was then warmed up to room temperature before 6-hydroxy-2-(methylthio)-4(1H)-pyrimidinone (25 g, 0.16 mol) was added in portions. The resultant reaction mixture was heated at 80° C. overnight followed by concentration under vacuum. The resulting slurry like residue was poured into ice, stirred for 2 hours then filtered to afford the crude product. The crude product was further purified by recrystalization with hexane to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (21.3 g, 61%). 1H-NMR (CDCl3) δ 2.66 (s, 3H), 10.4 (s, 1H).