Sodium borohydride → HCID 57460929, compound

HRID 1718947Notes

Reaction equation

HRID 1718947 reaction equation
[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[CH2:6]([C:10]1[N:11]=[C:12]([CH3:47])[N:13]([C:32]2[CH:46]=[CH:45][C:35]([O:36][C:37]([CH3:44])([CH3:43])[C:38](OCC)=[O:39])=[CH:34][CH:33]=2)[C:14](=[O:31])[C:15]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:19][CH:18]=1)[CH2:7][CH2:8][CH3:9]>O1CCCC1.C(O)C.C(OCC)(=O)C>[CH2:6]([C:10]1[N:11]=[C:12]([CH3:47])[N:13]([C:32]2[CH:33]=[CH:34][C:35]([O:36][C:37]([CH3:44])([CH3:43])[CH2:38][OH:39])=[CH:45][CH:46]=2)[C:14](=[O:31])[C:15]=1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:21][CH:22]=1)[CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57460927HCID 57460927, compound

Product 1

HCID 57460929HCID 57460929, compoundYield 61.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.85 g) was dissolved in tetrahydrofuran (20 mL) and ethanol (20 mL), and calcium chloride (1.2 g) was added at 0° C. The reaction solution was stirred at 0° C. for 1 hr, ethyl 2-{4-[4-butyl-5-[(2′-cyanobiphenyl-4-yl)methyl]-2-methyl-6-oxopyrimidin-1(6H)-yl]phenoxy}-2-methylpropanoate (2.1 g) was added, and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (1.2 g, 60%) as a pale-yellow liquid.

Workup

  1. stirringthe mixture was stirred overnight
  2. washwashed with 5% aqueous potassium hydrogen sulfate solution
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fe4e98f9667e47a69d3738cb56a486fe
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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