Sodium Carbonate → Cdc7-IN-15

A mixture of 6-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (522 mg, 2 mmol), tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.85 g, 6.00 mmol), cesium carbonate (3.26 g, 10.0 mmol), 1,2-dimethoxyethane (20 mL) and water (5 mL) was purged with argon. Then, 1,1′-bis(diphenylphosphino) ferrocenepalladium (II) dichloride dichloromethane adduct (163 mg, 0.20 mmol) was added, and the mixture was purged with argon again. The mixture was refluxed for 2 h. Then, sodium carbonate (636 mg, 6.00 mmol) was added. After 30 min, 8 M NaOH (1.5 mL, 12 mmol) was added. After 3 h, the mixture was cooled to room temperature, and poured into water (100 mL) and EtOAc (200 mL). The insoluble materials were filtered off, and the organic layer was collected from the filtrate. This organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc), then triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (312 mg, 60%) as a pale yellow solid:

1. customwas purged with argon
2. customthe mixture was purged with argon again
3. temperatureThe mixture was refluxed for 2 h
4. waitAfter 3 h
5. filtrationThe insoluble materials were filtered off
6. customthe organic layer was collected from the filtrate
7. washThis organic layer was washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc)
12. customtriturated with EtOAc
13. filtrationthe precipitate was collected by filtration

ORD record

ord-2c3f99d7a03447a09ef61d6fd6d41333

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691828B2