Methyl iodide → N-[4-Methyl-3-(1-methyl-7-methylsulfanyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide

HRID 2222253노트

반응식

HRID 2222253 반응식
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:6][C:5]=1[N:23]1[C:32](=[O:33])[C:31]2[C:26](=[N:27][C:28]([S:34][CH3:35])=[N:29][CH:30]=2)[NH:25][C:24]1=[O:36].I[CH3:38]>CN(C=O)C.C(OCC)(=O)C>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)=[CH:6][C:5]=1[N:23]1[C:32](=[O:33])[C:31]2[C:26](=[N:27][C:28]([S:34][CH3:35])=[N:29][CH:30]=2)[N:25]([CH3:38])[C:24]1=[O:36]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68522440N-[4-Methyl-3-(7-methylsulfanyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide

생성물 1

HCID 68527350N-[4-Methyl-3-(1-methyl-7-methylsulfanyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide수율 82%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To the suspension of NaH (60% dispersion in mineral oil, 19.7 mg, 0.49 mmol) in DMF is added N-[4-Methyl-3-(7-methylsulfanyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide (218 mg, 0.45 mmol) at 0° C. When H2 evolution has ceased, iodomethane (84 μl, 1.35 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 crystallized from MeOH to give N-[4-Methyl-3-(1-methyl-7-methylsulfanyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide (184 mg, 82%) as a white solid.

후처리

  1. washwashed with 5% aqueous Na2S2O3 solution
  2. customto remove DMF
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is crystallized from MeOH

출처 및 근거

ORD 기록
ord-e1216cf3cb4c4d9e91ef5c5ccc07fc40
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371750B2

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