4-Hydroxymethylpyridine → HCID 19787879、化合物

HRID 1656510ノート

反応式

HRID 1656510 の反応式
[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]

参加物

7

反応物 4

HCID 114724-HydroxymethylpyridineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 19787914HCID 19787914、化合物

生成物 1

HCID 19787879HCID 19787879、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-75d14d6d6c7144da94efdacd8b12f165
出典データセット
uspto-grants-1993_10
特許番号
US05254558

反応ノート

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