Water → 3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-methyl-1-[6-(2-nitro-phenylamino)-pyrimidin-4-yl]-urea

HRID 58128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58128
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[N:6]=[CH:5][N:4]=1.[H-].[Na+].[Cl:21][C:22]1[C:27]([N:28]=[C:29]=[O:30])=[C:26]([Cl:31])[C:25]([O:32][CH3:33])=[CH:24][C:23]=1[O:34][CH3:35].O>C1COCC1.CCOC(C)=O>[Cl:21][C:22]1[C:23]([O:34][CH3:35])=[CH:24][C:25]([O:32][CH3:33])=[C:26]([Cl:31])[C:27]=1[NH:28][C:29](=[O:30])[N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[N:6]=[CH:5][N:4]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 860869932,6-Dichloro-3,5-dimethoxyphenyl isocyanateHCID 118025224N-Methyl-N'-(2-nitro-phenyl)-pyrimidine-4,6-diamine

Produkt 1

HCID 1180245473-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-methyl-1-[6-(2-nitro-phenylamino)-pyrimidin-4-yl]-ureaAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-methyl-N′-(2-nitro-phenyl)-pyrimidine-4,6-diamine (150 g, 0.61 mmol) in THF (15 mL) was added NaH (60%, 60 g, 1.5 mmol) at 0° C., and the mixture was stirred for 30 minutes at room temperature. A solution of 2,4-dichloro-3-isocyanato-1,5-dimethoxy-benzene (180 g, 0.73 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 2 hours. Water (2 mL) was added to quench the reaction. The mixture was concentrated, and the residue was purified by flash chromatography on silica eluting with DCM:EtOAc=6:1-1:1 to obtain the title compound (54 mg, yield: 18%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 3.38 (s, 3H), 3.93 (s, 6H), 6.75 (s, 1H), 6.91 (s, 1H), 7.34 (t, 1H), 7.72 (t, 1H), 7.79 (d, 1H), 8.01 (d, 1H), 8.38 (s, 1H), 9.99 (s, 1H), 11.78 (s, 1H); MS (ESI): 493 [M+H]+.

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 2 hours
  2. customto quench
  3. customthe reaction
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by flash chromatography on silica eluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-033d91c61ff04380a99bdd5905795732
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

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