Ethyl Acetate → HCID 19702788, compound

HRID 861401Notes

Reaction equation

HRID 861401 reaction equation
CC1C([C:8]2[N:13]=[C:12]([C:14](F)(F)F)[C:11]([C:18]([C:20]3[C:21]([C:33]([F:36])([F:35])[F:34])=[N:22][C:23](C4C(C)=NC=NC=4)=[N:24][CH:25]=3)=[O:19])=[CH:10][N:9]=2)=CN=CN=1.[BH4-].[Na+].C(OC(=O)C)C.OP([O-])(O)=O.[K+]>C(O)C>[CH3:14][C:12]1[C:11]([CH:18]([C:20]2[C:21]([C:33]([F:36])([F:34])[F:35])=[N:22][CH:23]=[N:24][CH:25]=2)[OH:19])=[CH:10][N:9]=[CH:8][N:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516951Monobasic potassium phosphateHCID 4311764Sodium borohydrideHCID 54198393HCID 54198393, compound

Product 1

HCID 19702788HCID 19702788, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a cooled solution of 300 mg of (4-methylpyrimidin-5-yl)-4-trifluoromethylpyrimidin-5-yl ketone in 4.5 ml of ethanol (EtOH) was added 30 mg of sodium borohydride in 1 ml EtOH dropwise over a period of 20 minutes. After stirring at 0°-5° C. for another 10 minutes, ethylacetate (25 ml) and 15 ml of 10% KH2PO4 (pH=3) were added followed by vigorous stirring. The layers were separated and the aqueous extracted twice with dichloromethane-methanol (10:1). The organic layers were combined, dried (MgSO4) and stripped to yield 183 mg of 1-(4-methylpyrimidin-5-yl)-1-(4-trifluoromethylpyrimidin-5-yl)methanol.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous extracted twice with dichloromethane-methanol (10:1)
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ccaab8d83fb64cc5b8f31e0bca390f75
Source dataset
uspto-grants-1998_02
Patent number
US05714438

Reaction notes

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