Methyl iodide → 3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

HRID 2241232노트

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HRID 2241232 반응식
[C:1]1([NH:7][C:8]2[NH:13][C:12](=[O:14])[CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Li+].I[CH3:18]>CN(C=O)C>[CH3:18][N:13]1[C:12](=[O:14])[CH:11]=[CH:10][N:9]=[C:8]1[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 62714Lithium hydrideHCID 14038522-Anilino-4-hydroxypyrimidine

생성물 1

HCID 685179403-methyl-2-(phenylamino)pyrimidin-4(3H)-one수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(phenylamino)pyrimidin-4(3H)-one (0.250 g, 1.34 mmol) in DMF (10 mL) was added LiH (0.012 g, 1.47 mmol). The reaction mixture was stirred for 25 minutes and then iodomethane (0.166 mL, 2.67 mmol) was added. The reaction was stirred at room temperature for 18 hours, the quenched with H2O and partitioned between EtOAc and saturated aqueous NaCl. The phases were separated, and the aqueous phase was re-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude yellow oil. The crude product was purified by flash column chromatography, eluting with 30:1 dichloromethane/methanol. The desired product (0.166 g, 62%) was obtained as a white crystalline solid. 1H NMR (400 MHz, CDCl3) δ 7.68 (d, J=6.2 Hz, 1H), 7.46 (m, 2H), 7.39 (t, J=7.8 Hz, 2H), 7.19 (t, J=7.4 Hz, 1H), 6.48 (s, 1H), 6.01 (d, J=6.6 Hz, 1H), 3.58 (s, 3H). LRMS (ESI pos) m/e 202 (M+1).

후처리

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. customthe quenched with H2O
  3. custompartitioned between EtOAc and saturated aqueous NaCl
  4. customThe phases were separated
  5. extractionthe aqueous phase was re-extracted with EtOAc (1×)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a crude yellow oil
  10. customThe crude product was purified by flash column chromatography
  11. washeluting with 30:1 dichloromethane/methanol

출처 및 근거

ORD 기록
ord-0611399546a7499c9b8be79ad3059a16
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

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