Sodium Carbonate → 6-(2-fluoropyridin-4-yl)-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364009Notes

Reaction equation

Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[NH:5][C:4]=2[CH:3]=1.[F:14][C:15]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:14][C:15]1[CH:20]=[C:19]([C:2]2[S:10][C:9]3[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[NH:5][C:4]=3[CH:3]=2)[CH:18]=[CH:17][N:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.052 g, 0.20 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.085 g, 0.60 mmol), 2 M sodium carbonate (0.30 mL, 0.60 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane adduct (0.033 g, 0.040 mmol) in 1,4-dioxane (2 mL) was degassed with nitrogen and heated at 70° C. for 15 h. Then, the reaction was cooled to room temperature, and concentrated with silica gel (2 mL), and the residue was purified by flash chromatography (silica gel, ethyl acetate to 80:20 ethyl acetate/methanol) to give the title compound (0.038 g, 69%) as a yellow solid:

Workup

customwas degassed with nitrogen
temperatureThen, the reaction was cooled to room temperature
concentrationconcentrated with silica gel (2 mL)
customthe residue was purified by flash chromatography (silica gel, ethyl acetate to 80:20 ethyl acetate/methanol)

Sources & evidence

ORD record: ord-c4e725f8d6814af4a39884fc528f3038
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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