Sodium borohydride → (4-Methoxypyrimidin-2-yl)methanol

HRID 556375Notes

Reaction equation

HRID 556375 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][N:7]=1)=O)C.[BH4-].[Na+]>C(O)(C)(C)C>[CH3:13][O:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:4][OH:3])[N:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15880592HCID 15880592, compound

Product 1

HCID 13258428(4-Methoxypyrimidin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3.7 g (20.3 mMol) 4-methoxy-pyrimidine-2-carboxylic acid ethyl ester in 37 ml of tert-butanol, 2.3 g (61 mMol) of NaBH4 are added. The mixture is stirred at 60° C. for 5 h and cooled to rt. 15 min after quenching with 5 ml of acetone, the mixture is poured into 20 ml of a sat. NaHCO3 solution and 0.4 l EtOAc and stirred for 20 min. The inorganic phase is separated off and extracted twice with EtOAc. The organic layers are washed with 20 ml of a 1:1 mixture of brine and water, dried (Na2SO4) and concentrated, yielding (4-methoxy-pyrimidin-2-yl)-methanol (MS: [M+1]+=141).

Workup

  1. temperaturecooled to rt
  2. custom15 min after quenching with 5 ml of acetone
  3. additionthe mixture is poured into 20 ml of a sat. NaHCO3 solution and 0.4 l EtOAc
  4. stirringstirred for 20 min
  5. customThe inorganic phase is separated off
  6. extractionextracted twice with EtOAc
  7. washThe organic layers are washed with 20 ml of a 1:1 mixture of brine and water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8272c73313ed401aa0b22a45690f34eb
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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