Sodium Bicarbonate → Methyl 2-chloropyrimidine-4-carboxylate

HRID 232903Notes

Reaction equation

HRID 232903 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[CH:4][N:3]=1.[C:11]([O-])(O)=[O:12].[Na+]>CO>[CH3:11][O:12][C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)=[O:9]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 450814902-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 43811076Methyl 2-chloropyrimidine-4-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.5 g (2.82 mmol) of 2-chloropyrimidine-4-carboxylic acid chloride in 10 ml of methanol was stirred for 45 minutes at room temperature. Then the reaction solution was poured on 80 ml of saturated NaHCO3 solution and extracted three times with 50 ml of ethyl acetate each. The combined organic phase was washed with 60 ml of saturated NaCl solution, dried on Na2SO4 and concentrated by evaporation on a rotary evaporator. After drying on a high vacuum, 0.50 g of product was obtained as white solid, corresponding to a yield of 100 percent relative to the 2-chloropyrimidine-4-caboxylic acid chloride used. The melting point of the product was 93.6° to 96.6° C. Other data for the product was:

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate each
  2. washThe combined organic phase was washed with 60 ml of saturated NaCl solution
  3. customdried on Na2SO4
  4. concentrationconcentrated by evaporation on a rotary evaporator
  5. customAfter drying on a high vacuum

Sources & evidence

ORD record
ord-f98189b6414f4d59a1c31c0b18bf1cbc
Source dataset
uspto-grants-1997_01
Patent number
US05591853

Reaction notes

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