Sodium Carbonate → Methyl 2-[(5-bromopyrimidin-4-yl)sulfanyl]acetate

HRID 45783Notes

Reaction equation

HRID 45783 reaction equation
Cl[C:2]1[C:7]([Br:8])=[CH:6][N:5]=[CH:4][N:3]=1.[SH:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Br:8][C:7]1[C:2]([S:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:3][CH:4]=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 16907Methyl ThioglycolateHCID 122700785-Bromo-4-chloropyrimidine

Product 1

HCID 66318500Methyl 2-[(5-bromopyrimidin-4-yl)sulfanyl]acetateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-5-bromopyrimidine (0.193 g, 1.0 mmol), methyl 2-mercaptoacetate (0.116 g, 1.1 mmol) and sodium carbonate (0.159 g, 1.5 mmol) in DMF (0.7 mL) was heated under microwave irradiation to 150° C. for 20 minutes. The mixture was washed with water, extracted with ethyl acetate and purified by chromatography to yield methyl 2-(5-bromopyrimidin-4-ylthio)acetate (0.22 g, 84%).

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-401e8c061b314cfd83e39b36ef21ff42
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Reaction notes

Loading…