Dimethylformamide → (S)-7-chloro-5-((1-phenylethyl)thio)thiazolo[4,5-d]pyrimidin-2-amine

HRID 550762노트

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HRID 550762 반응식
O=P(Cl)(Cl)[Cl:3].CN(C=O)C.[NH2:11][C:12]1[S:13][C:14]2[C:19](O)=[N:18][C:17]([S:21][C@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])=[N:16][C:15]=2[N:30]=1>O1CCOCC1>[Cl:3][C:19]1[C:14]2[S:13][C:12]([NH2:11])=[N:30][C:15]=2[N:16]=[C:17]([S:21][C@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:23])[N:18]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychloride2회HCID 178462380HCID 178462380, 화합물

생성물 1

HCID 86622916(S)-7-chloro-5-((1-phenylethyl)thio)thiazolo[4,5-d]pyrimidin-2-amine수율 95%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

POCl3 (1 mL) was added to DMF (1 mL) in dioxane (6 mL). 2-Amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-ol (1 g, 3.3 mmol) was added to the reaction in one portion. POCl3 (1 mL) was added and the reaction mixture was heated to 80° C. for about 30 min. The reaction was cooled to room temperature and poured onto ice. The resulting mixture was heated at reflux for about 5 h. The mixture was allowed to attain room temperature and was then extracted with EtOAc. The organic layer was passed through a layer of silica gel and concentrated to dryness to give the title compound (1 g, 95% yield).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. additionpoured onto ice
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for about 5 h
  5. customto attain room temperature
  6. extractionwas then extracted with EtOAc
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-816fba36c88342c6a2966e13f3c9bad2
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947693B2

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