Methanol → Methyl 5-bromo-2-(methylsulfanyl)pyrimidine-4-carboxylate

HRID 1480802Notes

Reaction equation

HRID 1480802 reaction equation
[Br:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:18]O>>[Br:1][C:2]1[C:3]([C:10]([O:12][CH3:18])=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2917865-Bromo-2-(methylthio)pyrimidine-4-carboxylic Acid

Product 1

HCID 2794729Methyl 5-bromo-2-(methylsulfanyl)pyrimidine-4-carboxylateYield 80%

Procedure

A solution of 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (7.64 g, 30.7 mmol) in MeOH (60 mL) was treated with sulfuric acid (2 mL) and boiled for 24 hours. The mixture was poured onto ice water and extracted with DCM. The DCM phase was washed with saturated aqueous sodium hydrogen carbonate solution, dried and evaporated to give the title compound (6.42 g, 80%).

Workup

  1. additionThe mixture was poured onto ice water
  2. extractionextracted with DCM
  3. washThe DCM phase was washed with saturated aqueous sodium hydrogen carbonate solution
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-c92a055e3cb844518c1446f7b4dc1268
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…