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

HRID 1806521

반응식

HRID 1806521 반응식
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

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 6575TrichloroethyleneHCID 24813Phosphorus oxychlorideHCID 178503560HCID 178503560, 화합물

생성물 1

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

반응 조건

온도
80 °C

실험 절차

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 recrystallization with hexane to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (21.3 g, 61%).

후처리

  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 recrystallization with hexane

출처 및 근거

ORD 기록
ord-f8aad0a76a3c4409b17f033cec24ef3d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354416B2

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