Sodium borohydride → 4'-{[2-Ethyl-1-(4-{[1-(hydroxymethyl)cyclopentyl]oxy}phenyl)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile

HRID 1674237ノート

反応式

HRID 1674237 の反応式
[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[C:26](=[O:27])[N:25]([C:28]3[CH:43]=[CH:42][C:31]([O:32][C:33]4([C:38](OC)=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:30][CH:29]=3)[C:24]([CH2:44][CH3:45])=[N:23][C:22]=2[CH2:46][CH2:47][CH3:48])=[CH:16][CH:15]=1)#[N:7]>CO.O1CCCC1.C(OCC)(=O)C.Cl>[CH2:44]([C:24]1[N:25]([C:28]2[CH:43]=[CH:42][C:31]([O:32][C:33]3([CH2:38][OH:39])[CH2:34][CH2:35][CH2:36][CH2:37]3)=[CH:30][CH:29]=2)[C:26](=[O:27])[C:21]([CH2:20][C:17]2[CH:16]=[CH:15][C:14]([C:9]3[C:8]([C:6]#[N:7])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:19][CH:18]=2)=[C:22]([CH2:46][CH2:47][CH3:48])[N:23]=1)[CH3:45]

参加物

8

反応物 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57460881HCID 57460881、化合物

生成物 1

HCID 574608824'-{[2-Ethyl-1-(4-{[1-(hydroxymethyl)cyclopentyl]oxy}phenyl)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile収率 93%

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of sodium borohydride (0.39 g) in methanol (10 mL)-tetrahydrofuran (10 mL) was added calcium chloride (0.57 g) under ice-cooling, and the mixture was stirred for 15 min. A solution of methyl 1-{4-[5-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethyl-6-oxo-4-propylpyrimidin-1(6H)-yl]phenoxy}cyclopentanecarboxylate (0.94 g) in tetrahydrofuran (10 mL) was added, and the mixture was further stirred for 2 hr. Small pieces of ice were added in the reaction mixture and the mixture was stirred for 15 min. The mixture was diluted with ethyl acetate and 1 M hydrochloric acid. The organic layer was separated, washed with saturated sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (0.83 g, 93%) as a colorless solid.

後処理

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 2 hr
  3. additionSmall pieces of ice were added in the reaction mixture
  4. stirringthe mixture was stirred for 15 min
  5. customThe organic layer was separated
  6. washwashed with saturated sodium hydrogen carbonate and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-001a512f87b046cdb2f70f2e8175d9f6
出典データセット
uspto-grants-2011_08
特許番号
US07998968B2

反応ノート

読み込み中…