Sodium borohydride → (6-(Dimethylamino)-5-methylpyrimidin-4-yl)methanol

HRID 1753222Notes

Reaction equation

HRID 1753222 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9](OCC)=[O:10])[C:4]=1[CH3:14].[BH4-].[Na+]>CCO>[CH3:1][N:2]([CH3:15])[C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][OH:10])[C:4]=1[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117819038HCID 117819038, compound

Product 1

HCID 14306168(6-(Dimethylamino)-5-methylpyrimidin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 6-(dimethylamino)-5-methylpyrimidine-4-carboxylate (45) (60.0 g, 287.0 mmol) in EtOH (600 mL) was added in portionwise NaBH4 (21.82 g, 574.0 mmol) at 0° C. and the mixture was stirred for 16 h at RT. The solvent was evaporated under the reduced pressure and the reaction mixture was poured in to water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with water, brine, dried over sodium sulfate and concentrated at reduced pressure to yield (6-(dimethylamino)-5-methylpyrimidin-4-yl)methanol (46); 47 g, (97%).

Workup

  1. customThe solvent was evaporated under the reduced pressure
  2. additionthe reaction mixture was poured in to water (200 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-2016f5498e40433696c3493571859b57
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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