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

Temperature

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 record

ord-d37b30c099554f2d8ed235477210d40f

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06921763B2