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

HRID 222937

反応式

HRID 222937 の反応式
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

5

反応物 4

HCID 6228DimethylformamideHCID 6575TrichloroethyleneHCID 24813Phosphorus oxychlorideHCID 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).

後処理

  1. custombetween 5° C. to 10° C
  2. additionwas added in portions
  3. customThe resultant reaction mixture
  4. concentrationfollowed by concentration under vacuum
  5. additionThe resulting slurry like residue was poured into ice
  6. filtrationthen filtered
  7. customto afford the crude product
  8. customThe crude product was further purified by recrystalization with hexane

出典と根拠

ORDレコード
ord-161e5bdcdcef45a9b5b1e2e56d26460e
出典データセット
uspto-grants-2012_06
特許番号
US08207176B2

関連ノート

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