Cesium carbonate → 2-Chloro-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidine

HRID 56461Notes

Reaction equation

Br[C:2]1[CH:12]=[N:11][C:5]2[N:6]=[C:7]([Cl:10])[N:8]=[CH:9][C:4]=2[CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:10][C:7]1[N:8]=[CH:9][C:4]2[CH:3]=[C:2]([C:17]3[CH:16]=[C:15]([O:14][CH3:13])[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=3)[CH:12]=[N:11][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 6-bromo-2-chloropyrido[2,3-d]pyrimidine (800 mg, 3.3 mmol), 3,5-dimethoxyphenylboronic acid (655 mg, 3.6 mmol), bis(tri-tert-butylphosphine)palladium (83 mg, 0.16 mmol) and cesium carbonate (1.06 g, 3.3 mmol) in THF (30 mL) and water (6 mL) was degassed with nitrogen for three times and then heated at 85° C. for 0.5 hour. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/ethyl acetate=3/1) to get the title product as a yellow solid (460 mg, 47%) as a yellow solid. MS (ES+) C15H12ClN3O2 requires: 301, 302, found: 302, 304 [M+H]+.

Workup

customwas degassed with nitrogen for three times
temperatureThe mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (dichloromethane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-26556fabedf14c2b877808595e39c8bb
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434700B2

Reaction notes

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