Water → HCID 178437882, Verbindung

A mixture of 4-diethylaminomethyl benzoic acid hydrochloride (360 mg, 1.5 mmol), N,N'-carbonyldiimidazole (264 mg, 1.5 mmol) and dioxane (20 ml) was heated on an oil bath for 1 hour. The reaction mixture was cooled to room temperature and 1-cyclopentyl-3-ethyl-6-(4-hydroxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one (500 mg, 105 mmol) and dioxane (10 ml) were added and the reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled, the solvent was stripped and then water and ethyl acetate were added. The ethyl acetate layer was separated, then washed with 2N HCl (4×150 ml). The aqueous layers were combined, treated with concentrated NH4OH and then extracted with ethyl acetate (2×). The ethyl acetate layer was washed with brine, dried over MgSO4, filtered and stripped to afford crude product. The crude product was combined with the crude product from a similar experimental run and the mixture was recrystallized from ether to afford 0.46 g of 1-cyclopentyl-3-ethyl-6-[4-[4-(diethylaminomethyl)phenylcarbonyloxy]phenylmethyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 143°-145° C.

1. temperaturewas heated on an oil bath for 1 hour
2. temperaturethe reaction mixture was heated at 100° C. overnight
3. temperatureThe reaction mixture was cooled
4. customThe ethyl acetate layer was separated
5. washwashed with 2N HCl (4×150 ml)
6. additiontreated with concentrated NH4OH
7. extractionextracted with ethyl acetate (2×)
8. washThe ethyl acetate layer was washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customto afford crude product
12. customthe mixture was recrystallized from ether

ORD-Eintrag

ord-be35d3c4b26f45ec8707790a0d712094

Quelldatensatz

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05656629