Methyl iodide → 5-(1,1-Dimethylethyl) 4-methyl 6-methyl-4,5-pyrimidinedicarboxylate

HRID 227579

反応式

HRID 227579 の反応式
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].IC.[C:20](=O)([O-])[O-].[Li+].[Li+]>CN(C)C=O>[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:20])=[O:9])[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11125Lithium CarbonateHCID 671825105-(1,1-Dimethylethyl) hydrogen 6-methyl-4,5-pyrimidinedicarboxylate

生成物 1

HCID 671843365-(1,1-Dimethylethyl) 4-methyl 6-methyl-4,5-pyrimidinedicarboxylate収率 79.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 9.12 g (38 mmol) of the material from Step B in 100 mL of N,N-dimethyl formamide (DMF) was added 3.1 mL (50 mmol) of iodomethane and 3.7 g (50 mmol) of lithium carbonate. The reaction mixture was heated at 60° C. for 3 hours. After cooling the reaction mixture was partitioned between dichloromethane and water. The organic layer was dried (sodium sulfate) and the solvent was removed with a rotary evaporator and then a vacuum pump. The residue was purified by MPLC with a gradient of 20-30% ethyl acetate in hexanes as eluant to afford 7.58 g of the title compound as an off-white solid.

後処理

  1. temperatureAfter cooling the reaction mixture
  2. customwas partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customthe solvent was removed with a rotary evaporator
  5. customThe residue was purified by MPLC with a gradient of 20-30% ethyl acetate in hexanes as eluant

出典と根拠

ORDレコード
ord-945412e5f1a24566adb2db44b9eadcf2
出典データセット
uspto-grants-2009_07
特許番号
US07560564B2

関連ノート

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