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Methyl iodide → 7-methanesulfonyl-1-methyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 1988586
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HRID 1988586 반응식
[H-].[Na+].[CH3:3][S:4]([C:7]1[N:12]=[C:11]2[NH:13][C:14](=[O:27])[N:15]([C:17]3[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=3[CH3:26])[CH2:16][C:10]2=[CH:9][N:8]=1)(=[O:6])=[O:5].I[CH3:29]>CN(C=O)C.C(OCC)(=O)C>[CH3:3][S:4]([C:7]1[N:12]=[C:11]2[N:13]([CH3:29])[C:14](=[O:27])[N:15]([C:17]3[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=3[CH3:26])[CH2:16][C:10]2=[CH:9][N:8]=1)(=[O:5])=[O:6]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 597118317-methanesulfonyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

생성물 1

HCID 685260247-methanesulfonyl-1-methyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one수율 70.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To the suspension of NaH (60% dispersion in mineral oil, 139 mg, 3.5 mmol) in DMF is added 7-methanesulfonyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (1.15 g, 3.2 mmol), prepared as in Reference 1, at 0° C. When H2 evolution has ceased, iodomethane (0.99 ml, 15.8 mmol) is added and the reaction mixture is stirred for 3 hours at room temperature. The mixture is diluted with ethyl acetate, and washed with 5% aqueous Na2S2O3 solution to remove DMF. The organic layer is dried over MgSO4 and concentrated under reduced pressure. The crude product is purified by flash column chromatography (SiO2, EtOAc/hexane=1/1) to give 7-methanesulfonyl-1-methyl-3-(2-methyl-5-nitro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.85 g, 70%) as a white solid.

후처리

  1. additionis added
  2. customat 0° C
  3. washwashed with 5% aqueous Na2S2O3 solution
  4. customto remove DMF
  5. dry with materialThe organic layer is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by flash column chromatography (SiO2, EtOAc/hexane=1/1)

출처 및 근거

ORD 기록
ord-e0de0151e4884dae883a85fa2b06ffae
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07642255B2

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