Sodium borohydride → HCID 117819035, compound

HRID 1753225Notes

Reaction equation

HRID 1753225 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]([O-])=[O:11])[C:5]=1[CH3:13].[BH4-].[Na+]>C(O)C>[F:14][CH:2]([F:1])[O:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([CH2:10][OH:11])[C:5]=1[CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131733657HCID 131733657, compound

Product 1

HCID 117819035HCID 117819035, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 6-(difluoromethoxy)-5-methylpyrimidine-4-carboxylate 48b (14 g, 60.30 mmol) in ethanol (200 mL), NaBH4 (4.58 g, 120.59 mmol) was added at 0° C. and the mixture was stirred for 16 h at RT. Then the solvent was evaporated under the reduced pressure and the reaction mixture was poured in to water and extracted with ethyl acetate. The organic layer was washed with water brine and concentrated under reduced pressure to afford (6-(difluoromethoxy)-5-methylpyrimidin-4-yl)methanol 39 as a yellow solid. Yield: 8.4 g (73.3%).

Workup

  1. customThen the solvent was evaporated under the reduced pressure
  2. additionthe reaction mixture was poured in to water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water brine
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a959d61fc93a4004bf7d4b01cd9da1e0
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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