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 1988598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988598
[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]

Komponenten

6

Edukt 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

Produkt 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-benzamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9edd63d225dc47aba402fcff4c368a86
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642255B2

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