Acetone → HCID 178519775, compound

HRID 556379Notes

Reaction equation

HRID 556379 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([OH:12])[N:9]=[CH:8][N:7]=1)=O)C.[BH4-].[Na+].CC(C)=O>C(O)(C)(C)C>[OH:12][C:10]1[N:9]=[CH:8][N:7]=[C:6]([CH2:4][OH:3])[CH:11]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 178469368HCID 178469368, compound

Product 1

HCID 178519775HCID 178519775, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 1.7 g (10.1 mMol) 6-hydroxy-pyrimidine-4-carboxylic acid ethyl ester in 30 ml of tert-butanol, 1.2 g (31 mMol) of NaBH4 are added. The mixture is stirred at 60° C. for 20 h and cooled to rt. Then 45 ml of acetone are added. After stirring for 15 min, the mixture is concentrated in vacuo. The residue is diluted with toluene and again concentrated, yielding (6-hydroxy-pyrimidin-4-yl)-methanol (MS: [M−1]=125).

Workup

  1. additionare added
  2. temperaturecooled to rt
  3. stirringAfter stirring for 15 min
  4. concentrationthe mixture is concentrated in vacuo
  5. additionThe residue is diluted with toluene
  6. concentrationagain concentrated

Sources & evidence

ORD record
ord-e2a70db3a1184a15aa0cdf83d5627a1c
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

Loading…