Water → HCID 67958915, compound

HRID 707656Notes

Reaction equation

HRID 707656 reaction equation
[O:1]=[C:2]([C:4]1[CH:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[O:6][N:5]=1)[CH3:3].[BH4-].[Na+].O>CO>[OH:1][CH:2]([C:4]1[CH:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[O:6][N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67959197HCID 67959197, compound

Product 1

HCID 67958915HCID 67958915, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 2-(3-(1-oxo-ethyl)-isoxazol-5-yl)-pyrimidine (1.2 gm) in methanol (20 ml) was added sodium borohydride (0.485 gm) in lots at 0° C. It was stirred at 30° C. over a period of 2 h. The reaction mixture was evaporated under vacuum to provide a residue. The residue was stirred with water and extracted with ethyl acetate (25 ml X3). Combined organic layers was washed with aqueous sodium bicarbonate solution followed by water and concentrated under vacuum to provide title compound in 1.1 gm quantity (91%). It as used as without purification for the next reaction.

Workup

  1. customThe reaction mixture was evaporated under vacuum
  2. customto provide a residue
  3. extractionextracted with ethyl acetate (25 ml X3)
  4. washCombined organic layers was washed with aqueous sodium bicarbonate solution
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3b003fe7df0641cca606c7bcd617772c
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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