4-Hydroxymethylpyridine → HCID 19787879, 화합물

HRID 1656510노트

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HRID 1656510 반응식
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:27]([CH3:29])[CH3:28])[CH:14]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:4][CH:3]=1.Cl[C:37](Cl)([O:39][C:40](=[O:46])OC(Cl)(Cl)Cl)Cl.[N:48]1[CH:53]=[CH:52][C:51](CO)=[CH:50][CH:49]=1.C(=O)(O)[O-].[Na+]>ClCCl.C(N(CC)CC)C>[O:8]=[C:7]1[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:27]([CH3:29])[CH3:28])[CH:14]([O:19][Si:20]([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:21])[CH3:22])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[N:4][CH:3]=[C:2]1[NH:1][C:40]([O:39][CH2:37][C:51]1[CH:52]=[CH:53][N:48]=[CH:49][CH:50]=1)=[O:46]

참가 물질

7

반응물 4

HCID 114724-HydroxymethylpyridineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 19787914HCID 19787914, 화합물

생성물 1

HCID 19787879HCID 19787879, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

To a solution of 2-(5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (1.1 g) and triphosgene (0.93 g) in dichloromethane at 0° C. was added triethylamine (2.0 mL) and the resulting solution was allowed to stir for 0.5 h. To this solution was added 4-pyridylcarbinol and the resulting solution allowed to stir overnight. The solution was poured into saturated aqueous sodium bicarbonate solution and the product was extracted into dichloromethane. The organic solution was washed (saturated aqueous sodium bicarbonate, water), dried, and evaporated. The resulting oil was purified by chromatography, with methanol:dichloromethane (5:95) as the eluent, to provide 2-[6-oxo-2-phenyl-5-(4-pyridylmethoxycarbonylamino)-1,6-dihydro-1-pyrimidinyl]-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide as a white solid (0.9 g); TLC: Rf =0.4, methanol:dichloromethane (5:95).

후처리

  1. stirringto stir overnight
  2. extractionthe product was extracted into dichloromethane
  3. washThe organic solution was washed (saturated aqueous sodium bicarbonate, water)
  4. customdried
  5. customevaporated
  6. customThe resulting oil was purified by chromatography, with methanol:dichloromethane (5:95) as the eluent

출처 및 근거

ORD 기록
ord-75d14d6d6c7144da94efdacd8b12f165
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254558

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