Thionyl Chloride → 6-(Benzyloxy)-4-chloropyrido[3,4-d]pyrimidine

HRID 566390노트

반응식

HRID 566390 반응식
[CH2:1]([O:8][C:9]1[N:19]=[CH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16](O)[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:19]=[CH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16]([Cl:22])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 1785180356-phenylmethoxy-1H-pyrido[3,4-d]pyrimidin-4-one

생성물 1

HCID 227274286-(Benzyloxy)-4-chloropyrido[3,4-d]pyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide촉매

실험 절차

6-Benzyloxy-4-hydroxy-pyrido[3,4-d]pyrimidine (1.033 g, 4.1 mmol) was suspended in thionyl chloride (10 ml) under a nitogen atmosphere. DMF (3 drops) was added and the mixture was heated to reflux with stirring for 5.5 hours to give a dark solution, and then left to stand under nitrogen overnight. The mixture was concentrated in vacuo, azeotroping twice with toluene to remove all traces of thionyl cloride and acidic by-products. The material was further dried for two hours in vacuo to give the title compound as a brown solid, used without further purification; δH [2H6]DMSO 8.77(1H,s), 8.13(1H,s), 7.30-7.52 (6H,m), 5.45 (2H,s).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customto give a dark solution
  4. waitleft
  5. waitto stand under nitrogen overnight
  6. concentrationThe mixture was concentrated in vacuo
  7. customazeotroping twice with toluene
  8. customto remove all traces of thionyl cloride and acidic by-products
  9. customThe material was further dried for two hours in vacuo

출처 및 근거

ORD 기록
ord-3a7f5c11d6434fa980d7d4140415ba86
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174889B1

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