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 1674237노트

반응식

HRID 1674237 반응식
[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]

참가 물질

8

반응물 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57460881HCID 57460881, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-001a512f87b046cdb2f70f2e8175d9f6
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998968B2

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