Formic Acid → 2-(2,6-Dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine

HRID 2063515노트

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HRID 2063515 반응식
Cl[C:2]1[C:7]([NH:8][C:9](=O)[CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[C:6](Cl)[N:5]=[C:4]([S:21][CH3:22])[N:3]=1.NC(N)=[S:25].[CH3:27][CH2:28][OH:29].[CH:30]([OH:32])=O>>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[CH2:10][C:9]1[S:25][C:2]2[N:3]=[C:4]([S:21][CH3:22])[N:5]=[C:30]([OH:32])[C:7]=2[N:8]=1.[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[CH2:10][C:9]1[S:25][C:2]2[N:3]=[C:4]([S:21][CH3:22])[N:5]=[C:6]([O:29][CH2:28][CH3:27])[C:7]=2[N:8]=1

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 702EthanolHCID 2723790ThioureaHCID 57742481HCID 57742481, 화합물

생성물 2

HCID 685191702-(2,6-Dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine수율 41%HCID 178503525HCID 178503525, 화합물수율 18%

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온도
90 °C

실험 절차

To a mixture of N-(4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)-2-(2,6-dichloro-phenyl)-acetamide (10 g, 25 mmol), thiourea (1.9 g, 25 mmol), and EtOH (100 mL) was added formic acid (0.8 mL) at rt. The resulting mixture was heated to 90° C. After 12 h, the reaction mixture was cooled and concentrated. The resulting residue was collected by vacuum filtration and washed with H2O (50 mL) followed by hexanes (50 mL). The title compound purified by FCC to afford 2-(2,6-dichloro-benzyl)-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-7-ol (1.6 g, 18%) and 2-(2,6-dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine (4 g, 41%) as colorless solids.

후처리

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe resulting residue was collected by vacuum filtration
  4. washwashed with H2O (50 mL)
  5. customThe title compound purified by FCC

출처 및 근거

ORD 기록
ord-65a3cdb675ba47b286d6a3afb001b565
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288397B2

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