Ethyl Acetate → HCID 19702786, compound

HRID 861398Notes

Reaction equation

HRID 861398 reaction equation
C(C1C([C:9]2[N:14]=[C:13]([CH3:15])[C:12]([C:16]([C:18]3[C:19]([CH3:32])=[N:20][C:21](C4C(CC)=NC=NC=4)=[N:22][CH:23]=3)=[O:17])=[CH:11][N:10]=2)=CN=CN=1)C.[BH4-].[Na+].[CH3:35]COC(C)=O>CCO>[CH2:32]([C:19]1[C:18]([CH:16]([C:12]2[C:13]([CH3:15])=[N:14][CH:9]=[N:10][CH:11]=2)[OH:17])=[CH:23][N:22]=[CH:21][N:20]=1)[CH3:35]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 54086367HCID 54086367, compound

Product 1

HCID 19702786HCID 19702786, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 63 mg of (4-ethylpyrimidin-5-yl)-4-methylpyrimidin-5-yl ketone in 1 ml EtOH chilled in an ice bath was added 7.4 mg of sodium borohydride. After stirring the solution for 30 minutes, 1 ml of EtOAc was added followed by 1 ml NaH2PO4 (pH=3.0). The mixture was stirred vigorously and the aqueous extracted with EtOAc (3 times). The organic layers were combined, dried (MgSO4) and filtered through silica gel with EtOAc. The solvent was evaporated to yield 52 mg of pure 1-(4-ethylpyrimidin-5-yl)-1-(4-methylpyrimidin-5-yl)methanol.

Workup

  1. stirringThe mixture was stirred vigorously
  2. extractionthe aqueous extracted with EtOAc (3 times)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through silica gel with EtOAc
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d71a37ef3a754580a32349b2578dba7e
Source dataset
uspto-grants-1998_02
Patent number
US05714438

Reaction notes

Loading…