Water → 5-Bromo-2-chloro-4-(methylthio)pyrimidine

HRID 1674690Notes

Reaction equation

HRID 1674690 reaction equation
C(S)[CH2:2][S:3]([O-])(=O)=O.[Na+].[Br:9][C:10]1[C:11](Cl)=[N:12][C:13]([Cl:16])=[N:14][CH:15]=1.O>C(#N)C>[Br:9][C:10]1[C:11]([S:3][CH3:2])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 23662354Mesna

Product 1

HCID 122647965-Bromo-2-chloro-4-(methylthio)pyrimidineYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2 g of MeSNa (28.5 mmol; 1 eq.) and 6.5 g of 5-bromo-2,4-dichloropyrimidine (28.5 mmol, 1 eq.) were stirred in 50 mL dry acetonitrile at rt for 24 h. Then the mixture was poured into water, extracted with DCM, dried (Na2SO4) and evaporated to dryness. The product was recrystallized from hexane to yield 4 g of Intermediate 12 (70% yield).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried (Na2SO4)
  3. customevaporated to dryness
  4. customThe product was recrystallized from hexane

Sources & evidence

ORD record
ord-8771832bb2d54727880b4c4f54ed2595
Source dataset
uspto-grants-2011_08
Patent number
US08003655B2

Reaction notes

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