Methyl iodide → 2-benzyl-3-methyl-3H-pyrimidin-4-one

HRID 1993340ノート

反応式

HRID 1993340 の反応式
[C:1]([O-:4])([O-])=O.[Cs+].[Cs+].[CH2:7]([C:14]1[NH:19][C:18](=O)[CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CI>CN(C=O)C.C1COCC1>[CH2:7]([C:14]1[N:19]([CH3:18])[C:1](=[O:4])[CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 436545842-benzylpyrimidin-4(3H)-one

生成物 1

HCID 574453902-benzyl-3-methyl-3H-pyrimidin-4-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Cs2CO3 (24.6 g, 75.7 mmol) was added to 2-benzyl-3H-pyrimidin-4-one (Step 1, 12.8 g) in DMF (80 mL) and THF (60 mL) at 0° C. After 10 min, MeI (4.3 mL, 68.8 mmol) was added, and the reaction was warmed to RT. After 3 h, the reaction was decanted, diluted with CH2Cl2, and washed with H2O, and aq. sat. NaCl solution. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Et2O and Hexane (1:1) were added and the solvent was evaporated to provide a brown solid. The solid was triturated with 30′ EtOAc/hexane to afford the title compound as a light brown solid. The filtrate was purified by chromatography with 0-5% MeOH/CHCl3 to afford additional compound. MS (ESI pos. ion) m/z: 201.0. (M+H). Calc'd for C12H12N2O: 200.09.

後処理

  1. waitAfter 3 h
  2. customthe reaction was decanted
  3. additiondiluted with CH2Cl2
  4. washwashed with H2O, and aq. sat. NaCl solution
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. additionEt2O and Hexane (1:1) were added
  8. customthe solvent was evaporated
  9. customto provide a brown solid
  10. customThe solid was triturated with 30′ EtOAc/hexane

出典と根拠

ORDレコード
ord-52f23a1ca5e843e9bc2f695d296ebcf4
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

反応ノート

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