Ethanol hydrochloride → HCID 20738507, compound

HRID 354003Notes

Reaction equation

HRID 354003 reaction equation
[Br:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.Cl.[CH3:14][CH2:15]O>>[CH2:14]([O:11][C:10]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([CH2:8][OH:9])[N:4]=1)=[O:12])[CH3:15]

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 23512555HCID 23512555, compound

Product 1

HCID 20738507HCID 20738507, compoundYield 80%

Procedure

A solution of 4.2 g (18.02 mmol) 5-bromo-2-hydroxymethyl-pyrimidine-4-carboxylic acid in 50 ml 5N HCl/EtOH was stirred for 5 hrs. at RT. After evaporation of the solvent the residue was distributed between 50 ml CH2Cl2 and 30 ml H2O. The organic phase was washed with sat. NaHCO3 and brine. The combined organic phases were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography to give 3.80 g (80%) 5-bromo-2-hydroxymethyl-pyrimidine-4-carboxylic acid ethyl ester as a pale yellow solid.

Workup

  1. customat RT
  2. customAfter evaporation of the solvent the residue
  3. washThe organic phase was washed with sat. NaHCO3 and brine
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-577aa4f161b840bea9eda4e06d2d7514
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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