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

HRID 604676

反応式

HRID 604676 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-23d860eb7f564aafaa18d468aec107e6
出典データセット
uspto-grants-2011_03
特許番号
US07910592B2

関連ノート

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