Water → 3-Methyl-2-(methylthio)-4(3H)-pyrimidinone

HRID 1993344

반응식

HRID 1993344 반응식
[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[Li+].[CH3:11][Si]([N-][Si](C)(C)C)(C)C.CI.O>CN(C=O)C>[CH3:11][N:8]1[C:7](=[O:9])[CH:6]=[CH:5][N:4]=[C:3]1[S:2][CH3:1]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 798232-(Methylthio)-1H-pyrimidin-4-oneHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 1387273-Methyl-2-(methylthio)-4(3H)-pyrimidinone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

2-Methylthio-3H-pyrimidin-4-one (Step 1, 6.29 g, 44.2 mmol) was suspended in DMF (100 mL), cooled to 0° C., and additional DMF (50 mL) was added. Solid LiHMDS (9.58 g, 57.3 mmol) was added in one portion, and the reaction was stirred at 0° C. MeI (3.6 mL, 57.8 mmol) was added via syringe, and the reaction was warmed to RT and stirred for 20.75 h. At this time, the mixture was poured into 300 mL H2O and extracted exhaustively with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered, concentrated, and purified on silica gel (3:1→3:2→1:1 hexanes/EtOAc) to give the title compound. MS (ESI pos. ion) m/z: 157. Calc'd for C6H8N2OS: 156.04.

후처리

  1. temperaturethe reaction was warmed to RT
  2. stirringstirred for 20.75 h
  3. extractionextracted exhaustively with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel (3:1→3:2→1:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-659dea8943cd4f6a92aba0c5d25cfd6a
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652009B2

연결된 노트

불러오는 중…