Imidazole → HCID 58507769, 화합물

HRID 253021노트

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HRID 253021 반응식
[N:1]1([C:7]2[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C=O)C>[C:31]([Si:28]([CH3:30])([CH3:29])[O:19][C:15]1[CH:14]=[C:13]([C:11]2[N:12]=[C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=2)[CH:18]=[CH:17][CH:16]=1)([CH3:34])([CH3:33])[CH3:32]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 99013723-(4-Morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)phenol

생성물 1

HCID 58507769HCID 58507769, 화합물수율 83.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A mixture of 3-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenol (17.28 g, 55.1 mmol), imidazole (1.7 eq., 93.7 mmol, 6.38 g) and tert-butyldimethylsilyl chloride (1.5 eq., 82.7 mmol. 12.47 g) in DMF (45 mL) was heated at 50° C. for 5 hours. The reaction mixture was then cooled and partitioned between water (400 mL) and ether (3×400 mL). The combined organic layers were washed sequentially with saturated aqueous sodium hydrogen carbonate (300 mL), brine (300 mL), separated and dried (MgSO4). The crude product was evaporated onto silica and purified by chromatography (5%→20% ethyl acetate-petrol) to yield compound 7 as a white solid (19.60 g, 83%).

후처리

  1. temperatureThe reaction mixture was then cooled
  2. custompartitioned between water (400 mL) and ether (3×400 mL)
  3. washThe combined organic layers were washed sequentially with saturated aqueous sodium hydrogen carbonate (300 mL), brine (300 mL)
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. customThe crude product was evaporated onto silica
  7. custompurified by chromatography (5%→20% ethyl acetate-petrol)

출처 및 근거

ORD 기록
ord-b917dea8f2c34f5abb91add11e1aa07a
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872003B2

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