Methyl iodide → 2-amino-6-(2,6-dichlorophenyl)-8-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1586408

Reaktionsgleichung

[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([OH:20])=[N:8][C:6]=2[N:7]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9](=[O:20])[N:8]([CH3:23])[C:6]=2[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

To a mixture of 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol (3.7 g) from Example 11 in dimethylformamide was added NaH (50% suspension in mineral oil, 0.64 g). The resulting slurry was heated at 65° C. for 0.5 hour until a solution formed. It was then cooled to 50° C. and a solution of methyl iodide (2.0 g) in dimethylformamide (10 mL) was added dropwise to the reaction. The reaction mixture was warmed and kept between 60° C.-80° C. for 3 hours. Upon cooling to room temperature, the reaction mixture was poured into ice water. The insoluble white product was filtered, washed with water, and recrystallized from ethanol using charcoal to give 1.9 g of 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7(8H)-one; mp 235-237° C.

Aufarbeitung

customformed
temperatureIt was then cooled to 50° C.
temperatureThe reaction mixture was warmed
temperatureUpon cooling to room temperature
filtrationThe insoluble white product was filtered
washwashed with water
customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-e84c2b556c814c8487e22a7a08a74aa6
Quelldatensatz: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05945422

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