Water → N-{3-[7-(3-tert-butyl-ureido)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl]-2,4-dichloro-phenyl}-3-trifluoromethyl-benzamide

HRID 252196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252196
[NH2:1][C:2]1[C:3]([C:14]2[C:15]([Cl:34])=[C:16]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:17]=[CH:18][C:19]=2[Cl:20])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[N:13]=1.[H-].[Na+].[C:37]([N:41]=[C:42]=[O:43])([CH3:40])([CH3:39])[CH3:38].O>CN(C=O)C>[C:37]([NH:41][C:42](=[O:43])[NH:1][C:2]1[C:3]([C:14]2[C:15]([Cl:34])=[C:16]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:17]=[CH:18][C:19]=2[Cl:20])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[N:13]=1)([CH3:40])([CH3:39])[CH3:38]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62412tert-Butyl isocyanateHCID 59833927HCID 59833927, Verbindung

Produkt 1

HCID 59860301N-{3-[7-(3-tert-butyl-ureido)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl]-2,4-dichloro-phenyl}-3-trifluoromethyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N—[3-(7-amino-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl)-2,4-dichloro-phenyl]-3-trifluoromethyl-benzamide (700 mg, 1.34 mmol) in dry DMF (10 ml) at 0° C. is added NaH (60% oil suspension, 64 mg, 1.6 mmol) slowly. The reaction mixture is stirred at room temperature for 30 minutes and then to this reaction mixture t-butyl-isocyanate (0.19 ml, 1.6 mmol) is added. The reaction is stirred at room temperature for 5 hours. The reaction mixture is diluted into 100 ml water, extracted with 80 ml ethyl acetate three times. The organic phase is combined and washed with brine, dried over Na2SO4. The crude product is purified by flash silica gel column to give the title compound as light yellow solid.

Aufarbeitung

  1. stirringThe reaction is stirred at room temperature for 5 hours
  2. extractionextracted with 80 ml ethyl acetate three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product is purified by flash silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-98ee21a0102a470a94288c606ca82a76
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868018B2

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