Potassium Carbonate → 6-(6-Methoxypyridin-3-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 472205Notes

Reaction equation

Br[C:2]1[C:14](=[O:15])[NH:13][C:5]2[N:6]=[C:7]([S:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.[CH3:16][O:17][C:18]1[N:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:16][O:17][C:18]1[N:23]=[CH:22][C:21]([C:2]2[C:14](=[O:15])[NH:13][C:5]3[N:6]=[C:7]([S:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=3[CH:3]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (50 mg, 0.17 mmol), 6-methoxypyridin-3-ylboronic acid (40.1 mg, 1.1 equiv), dichlorobis(triphenylphosphine) palladium(II) (6.13 mg, 0.008 mmol), DMF (2 mL) in a 5 mL microwave vial was added potassium carbonate (3 M, 1.1 equiv). The solution was degassed with N2 for 10 min before being capped and heated in the microwave reactor for 1 h. at 100° C. The reaction was poured into 20 ml brine and the precipitate was collected by filtration. It was further purified by chromatography (80% thylacetate/hexane). The title compound was obtained as a solid (30 mg, 55% yield).

Workup

customThe solution was degassed with N2 for 10 min
custombefore being capped
additionThe reaction was poured into 20 ml brine
filtrationthe precipitate was collected by filtration
customIt was further purified by chromatography (80% thylacetate/hexane)

Sources & evidence

ORD record: ord-51a5bdd41cac40aa9d0fb1040ba67a3a
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633204B2

Reaction notes

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