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

HRID 227579

반응식

HRID 227579 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-945412e5f1a24566adb2db44b9eadcf2
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560564B2

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