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

HRID 604676

Reaction equation

HRID 604676 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.[CH3:13][Si](C=[N+]=[N-])(C)C>CO>[Br:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 2917865-Bromo-2-(methylthio)pyrimidine-4-carboxylic Acid

Product 1

HCID 2794729Methyl 5-bromo-2-(methylsulfanyl)pyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (2 g, 8.03 mmol) was stirred in MeOH (40 mL) at room temperature. To this stirred mixture was added (trimethylsilyl)diazomethane (12.04 mL, 2M, 24-09 mmol). LCMS of aliquot taken immediately after addition indicated there was still unreacted starting acid. Added more (trimethylsilyl)diazomethane (6 mL, 2 M, 12 mmol). LCMS indicated completion of reaction. The reaction was quenched adding about 0.5 mL of TFA into the crude mixture. Volatiles were removed under reduced pressure. The resulting crude mixture was purified by flash chromatography (SiO2, Biotage 40M cartridge). The column was eluted with a EtOAc/hexanes gradient mixture (0% to 30%). Related fraction were pooled and evaporated to afford a colorless crystalline solid as the titled compound. LCMS calc.=263.94; found=264.79.

Workup

  1. additionafter addition
  2. customcompletion of reaction
  3. customThe reaction was quenched
  4. additionadding about 0.5 mL of TFA into the crude mixture
  5. customVolatiles were removed under reduced pressure
  6. customThe resulting crude mixture was purified by flash chromatography (SiO2, Biotage 40M cartridge)
  7. washThe column was eluted with a EtOAc/hexanes gradient mixture (0% to 30%)
  8. customevaporated

Sources & evidence

ORD record
ord-23d860eb7f564aafaa18d468aec107e6
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Linked notes

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