Water → tert-Butyl (6-(hydroxymethyl)pyrimidin-4-yl)carbamate

HRID 2366181Notes

Reaction equation

HRID 2366181 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:4]=1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23593604Tert-butyl (6-formylpyrimidin-4-yl)carbamate

Product 1

HCID 72698493tert-Butyl (6-(hydroxymethyl)pyrimidin-4-yl)carbamateYield 31.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the crude tert-butyl 6-formylpyrimidin-4-ylcarbamate (4.6 g, 0.020 mol) in MeOH (100 mL) was added sodium borohydride (0.74 g, 0.020 mol) in four portions at room temperature. After addition, the resulting mixture was stirred for 1 hour and then water (50 mL) was added. The solvent was removed under reduced pressure and the resulting aqueous residue was extracted with EtOAc (3×100 mL). The combined organic extract was washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified via silica gel column chromatography, eluting with DCM/MeOH (30:1) to give the desired product (1.4 g, 30% yield). LCMS (ESI) m/z: 226.0 [M+H+].

Workup

  1. additionAfter addition
  2. customThe solvent was removed under reduced pressure
  3. extractionthe resulting aqueous residue was extracted with EtOAc (3×100 mL)
  4. extractionThe combined organic extract
  5. washwas washed with water (30 mL) and brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via silica gel column chromatography
  9. washeluting with DCM/MeOH (30:1)

Sources & evidence

ORD record
ord-75da38fcc33842cf87c722e62493f4b2
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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