Water → 2-[(4,4-difluorocyclohexyl)oxy]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 570698ノート

反応式

HRID 570698 の反応式
[H-].[Na+].[F:3][C:4]1([F:11])[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1.C(S[C:16]1[N:17]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[CH:30][CH:29]=2)[C:18](=[O:27])[C:19]2[CH:25]=[CH:24][C:23](=[O:26])[NH:22][C:20]=2[N:21]=1)CC.O>O1CCCC1>[F:3][C:4]1([F:11])[CH2:9][CH2:8][CH:7]([O:10][C:16]2[N:17]([C:28]3[CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[CH:32][CH:33]=3)[C:18](=[O:27])[C:19]3[CH:25]=[CH:24][C:23](=[O:26])[NH:22][C:20]=3[N:21]=2)[CH2:6][CH2:5]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5463004,4-Difluorocyclohexan-1-olHCID 866853582-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

生成物 1

HCID 866853612-[(4,4-difluorocyclohexyl)oxy]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione収率 39.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of sodium hydride (60% in oil, 19 mg) in tetrahydrofuran (5 ml) was added 4,4-difluorocyclohexanol (109 mg) at room temperature, and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added 2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (165 mg), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and recrystallized from a mixed solvent of hexane/ethyl acetate to give the title compound (75 mg).

後処理

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customrecrystallized from a mixed solvent of hexane/ethyl acetate

出典と根拠

ORDレコード
ord-c4fae2e23e474d01a37369442636685e
出典データセット
uspto-grants-2015_05
特許番号
US09023858B2

反応ノート

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