1,2-Dimethoxyethane → HCID 66743326, compound

Temperature

90 °C

A mixture of 6-bromo-1,2,2,7-tetramethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (145 mg, 0.50 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-1-carboxylate (441 mg, 1.50 mmol), cesium carbonate (815 mg, 2.50 mmol), 1,2-dimethoxyethane (5 mL) and water (1.25 mL) was purged with argon. Then, 1,1′-bis(diphenylphosphino) ferrocenepalladium (II) dichloride dichloromethane adduct (40.8 mg, 0.050 mmol) was added, and the mixture was purged with argon again. The mixture was stirred at 90° C. overnight. The mixture was poured into water (100 mL) and EtOAc (100 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 and concentrated under reduced pressure. The residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc then to 80:20 EtOAc/MeOH), then triturated with EtOAc/hexane. The solid was collected by filtration to afford the title compound (65.2 mg, 47%) as a white solid:

1. customwas purged with argon
2. customthe mixture was purged with argon again
3. additionThe mixture was poured into water (100 mL) and EtOAc (100 mL)
4. filtrationThe insoluble materials were filtered off
5. customthe organic layer was collected from the filtrate
6. washThis organic layer was washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc
10. customto 80:20 EtOAc/MeOH), then triturated with EtOAc/hexane
11. filtrationThe solid was collected by filtration

ORD record

ord-ccbdd5de63e04517968925da696703fd

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691828B2