N,N-Dimethylaniline → 7-Chloro-2-(difluoromethyl)-[1,3]thiazolo[5,4-d]pyrimidine

HRID 930440노트

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HRID 930440 반응식
[F:1][CH:2]([F:13])[C:3]1[S:4][C:5]2[N:6]=[CH:7][N:8]=[C:9](O)[C:10]=2[N:11]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[Cl:25][C:9]1[C:10]2[N:11]=[C:3]([CH:2]([F:13])[F:1])[S:4][C:5]=2[N:6]=[CH:7][N:8]=1

참가 물질

5

반응물 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178518072HCID 178518072, 화합물

생성물 1

HCID 867322777-Chloro-2-(difluoromethyl)-[1,3]thiazolo[5,4-d]pyrimidine

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

A mixture of 2-(difluoromethyl)thiazolo[5,4-d]pyrimidin-7-ol, N,N-dimethylaniline (0.800 mL, 6.31 mmol) and phosphorus oxychloride (6.00 mL, 65.5 mmol) in toluene (20 mL) was heated at 80° C. for 6 h. The reaction mixture was cooled of rt and the solvent removed invacuo. The residue was dissolved in DCM, evaporated onto silica gel and purified by flash chromatography (Isco (80 gram)) eluting with (EtOAc):hexanes (0:1→1:3) to give an off-white crystalline solid (252 mg, 18% over 2 steps). MS m/z=221.9, 223.9 [M+H]+. Calculated for C6H2F2N3S: 221.

후처리

  1. temperatureThe reaction mixture was cooled of rt
  2. customthe solvent removed invacuo
  3. dissolutionThe residue was dissolved in DCM
  4. customevaporated onto silica gel
  5. custompurified by flash chromatography (Isco (80 gram))
  6. washeluting with (EtOAc)
  7. customhexanes (0:1→1:3) to give an off-white crystalline solid (252 mg, 18% over 2 steps)

출처 및 근거

ORD 기록
ord-e75fe65d87614407ae8c605a5d82d42e
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296734B2

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