Dimethylformamide → 7-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reaktionsgleichung

[NH:1]([C:3]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:7](=[O:18])[N:6]([CH3:19])[C:5](=[O:20])[CH:4]=1)[NH2:2].O=P(Cl)(Cl)Cl.[CH3:26]N(C=O)C>>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]2[C:3]3[NH:1][N:2]=[CH:26][C:4]=3[C:5](=[O:20])[N:6]([CH3:19])[C:7]2=[O:18])=[CH:11][CH:12]=1

Komponenten

Edukt 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 667954896-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 685009507-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneAusbeute 90 %

Versuchsvorschrift

To a solution of 6-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (4.0 g, 14.5 mmol) in anhydrous DMF (200 mL) is added POCl3 (16 mL) dropwise with IPA-dry ice bath cooling. After the completion of the addition, the mixture is allowed to warm up to room temperature and stirred at r.t. overnight. DMF is removed under reduced pressure, and the residue is treated with cold water very carefully. The generated precipitate is filtered, washed with water to give pure product as white solids (3.74 g, yield: 90%). MS (ESI) m/z 287.1 [M+H]+