Water → 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

A degassed mixture of potassium acetate (1.9 g, 19 mmol), PdCl2(PtBu2Ph)2 (0.16 g, 0.26 mmol), 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (1.00 g, 6.5 mmol) and 2-fluoropyridin-3-ylboronic acid (1.1 g, 7.8 mmol) in EtOH (30 mL)-water (10 mL) was sonicated until the solid became a fine powder. The mixture was refluxed under N2 overnight. After cooling to rt, solvent was removed in vacuo and water (50 mL) and NaHCO3 (sat. 100 mL) were added to the residue. The mixture was extracted with EtOAc (3×100 mL). The solid was filtered and washed with water. The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered through celite and concentrated in vacuo to give 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (0.56 g). The previous solid was dissolved in MeOH-DCM and preloaded on silica gel and purified by flash column chromatography eluting with MeOH/DCM (1-5%) to give give 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (3.4 g). The two product crops were combined (65% overall). MS (ESI, pos. ion) m/z: 216 [M+H]+

1. customwas sonicated until the solid
2. temperatureThe mixture was refluxed under N2 overnight
3. customsolvent was removed in vacuo and water (50 mL) and NaHCO3 (sat. 100 mL)
4. additionwere added to the residue
5. extractionThe mixture was extracted with EtOAc (3×100 mL)
6. filtrationThe solid was filtered
7. washwashed with water
8. washThe combined organic layers were washed with brine (50 mL)
9. dry with materialdried over MgSO4
10. filtrationfiltered through celite and
11. concentrationconcentrated in vacuo

ORD record

ord-0db3b274a8b74002b1074dc23383c57d

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557830B2