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

HRID 2241232ノート

反応式

HRID 2241232 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0611399546a7499c9b8be79ad3059a16
出典データセット
uspto-grants-2010_05
特許番号
US07723330B2

反応ノート

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