Sodium hydride → methyl 5-[4-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenoxy]-2-furoate

Temperatur

90 °C

A mixture of 4-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol (0.107 g, 0.362 mmol, 1.0 equiv), DMSO (0.5 mL), sodium hydride (60%, 0.030 g, 0.72 mmol, 2.0 equiv), and methyl-5-nitro-2-furoate (0.062 g, 0.36 mmol, 1.0 equiv) was heated at 90° C. for 3 h. The reaction mixture was allowed to cool to room temperature, poured into ice water (10 mL), and extracted with three portions of CH2Cl2 (50 mL each). The combined organic extracts were washed with 5% aqueous KOH (50 mL) and the organic layer was dried over MgSO4, filtered, and concentrated to afford a red oil which was purified by column chromatography on silica gel (elution with 300 mL of 5% MeOH/CH2Cl2) to afford methyl 5-[4-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenoxy]-2-furoate as a red solid (0.070 g, 0.17 mmol):

1. temperatureto cool to room temperature
2. extractionextracted with three portions of CH2Cl2 (50 mL each)
3. washThe combined organic extracts were washed with 5% aqueous KOH (50 mL)
4. dry with materialthe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto afford a red oil which
8. customwas purified by column chromatography on silica gel (elution with 300 mL of 5% MeOH/CH2Cl2)

ORD-Eintrag

ord-682ca9f8e0214990b3e74b415efc9637

Quelldatensatz

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06660744B1