Sodium borohydride → HCID 57460879, compound

HRID 1718904Notes

Reaction equation

HRID 1718904 reaction equation
[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:45]=[CH:44][C:31]([O:32][CH:33]4[CH2:38][CH2:37][CH:36]([C:39](OCC)=[O:40])[CH2:35][CH2:34]4)=[CH:30][CH:29]=3)[C:24]([CH2:46][CH3:47])=[N:23][C:22]=2[CH2:48][CH2:49][CH3:50])=[CH:16][CH:15]=1)#[N:7]>C(O)C.O1CCCC1.C(OCC)(=O)C.Cl>[CH2:46]([C:24]1[N:25]([C:28]2[CH:45]=[CH:44][C:31]([O:32][CH:33]3[CH2:34][CH2:35][CH:36]([CH2:39][OH:40])[CH2:37][CH2:38]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]([CH2:48][CH2:49][CH3:50])[N:23]=1)[CH3:47]

Participants

8

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57460878HCID 57460878, compound

Product 1

HCID 57460879HCID 57460879, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium borohydride (0.85 g) in ethanol (10 mL)-tetrahydrofuran (10 mL) was added calcium chloride (1.3 g) under ice-cooling, and the mixture was stirred for 15 min. A solution of ethyl 4-{4-[5-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethyl-6-oxo-4-propylpyrimidin-1(6H)-yl]phenoxy}cyclohexanecarboxylate (1.7 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 and 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 (1.1 g, 71%) as a solid.

Workup

  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

Sources & evidence

ORD record
ord-639c72bd606d497f83ed82a3274d43b8
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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