Potassium Carbonate → 4,6-Dimethoxy-5-(pyridin-4-yl)pyrimidine

HRID 271453Notes

Reaction equation

Br[C:2]1[C:3]([O:10][CH3:11])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH3:9].[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.C1COCC1>[CH3:11][O:10][C:3]1[C:2]([C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)=[C:7]([O:8][CH3:9])[N:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-bromo-4,6-dimethoxypyrimidine (2.18 g, 10 mmol), pyridine-4-boronic acid (1.85 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), and PXPd (539 mg, 1.0 mmol) in ethanol/THF (1:1, 25 mL) under argon was heated at 70° C. for 3 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, the solvent mixture was removed under reduced pressure. The residue was dissolved in EtOAc (30 mL) and washed with saturated aqueous NaCl (20 mL), then dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain the title compound (1.79 g) as a white solid. 1H NMR (CDCl3): δ 3.97 (s, 6H), 7.36 (d, 2H), 8.47 (s, 1H), 8.64 (d, 2H).

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customthe solvent mixture was removed under reduced pressure
dissolutionThe residue was dissolved in EtOAc (30 mL)
washwashed with saturated aqueous NaCl (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated under reduced pressure
customThe crude product was purified by silica gel column chromatography
washeluted with ethyl acetate-hexanes

Sources & evidence

ORD record: ord-d3057b90c0c9415eb0cf0bd0d9f9ec7e
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452892B2

Reaction notes

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