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

HRID 604676

반응식

HRID 604676 반응식
[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

참가 물질

4

반응물 2

HCID 167693Trimethylsilyldiazomethane2회HCID 2917865-Bromo-2-(methylthio)pyrimidine-4-carboxylic Acid

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23d860eb7f564aafaa18d468aec107e6
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

연결된 노트

불러오는 중…