(3-methylphenyl)methanesulfonyl Chloride → 5-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide

HRID 1409591

Reaktionsgleichung

Reaktionsgleichung von HRID 1409591
CC(C)([O-])C.[K+].[NH2:7][C:8]1[N:9]([CH3:27])[C:10](=[O:26])[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]([NH:16][CH3:17])=[O:15])[N:13]=1.[CH3:28][C:29]1[CH:30]=[C:31]([CH2:35][S:36](Cl)(=[O:38])=[O:37])[CH:32]=[CH:33][CH:34]=1>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH3:17][NH:16][C:14]([C:12]1[N:13]=[C:8]([NH:7][S:36]([CH2:35][C:31]2[CH:30]=[C:29]([CH3:28])[CH:34]=[CH:33][CH:32]=2)(=[O:38])=[O:37])[N:9]([CH3:27])[C:10](=[O:26])[C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:15]

Komponenten

7

Edukt 3

HCID 2760662(3-methylphenyl)methanesulfonyl Chloride2×HCID 23665647Potassium tert-butoxideHCID 86710289HCID 86710289, Verbindung

Produkt 1

HCID 867102905-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamideAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium tert-butoxide (75.9 mg, 676 μmol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (150 mg, 520 μmol) in THF (15.0 ml) and DMF (3 ml). The resulting mixture was stirred for 10 min and then cooled with an ice-bath. To this mixture was slowly added a solution of (3-methylphenyl)methanesulfonyl chloride (140 mg, 684 μmol) in THF (1 ml). The reaction mixture was stirred at room temperature overnight. A further solution of (3-methylphenyl)methanesulfonyl chloride (140 mg, 684 μmol) in THF (1 ml) was added and then the mixture was stirred at room temperature for 48 hours. The resulting mixture was diluted with EtOAc, washed with saturated NaHCO3 aqueous solution and brine. The organic layers were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (silica gel, 0% to 2% MeOH in DCM) provided the desired product as a light yellow solid (0.070 g; 29%). LCMS: m/z=457 (MH+).

Aufarbeitung

  1. temperaturecooled with an ice-bath
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. stirringthe mixture was stirred at room temperature for 48 hours
  4. washwashed with saturated NaHCO3 aqueous solution and brine
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6e6c9378a7ff45c288cd8399662c0aae
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921388B2

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