Water → HCID 86682473, compound

HRID 715909Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)=[O:18].O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([C:17]([O:16][CH3:15])=[O:18])[CH:24]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1.93 g (10.0 mmol) of 2-chloro-5-bromopyrimidine in 30 ml of toluene, 4.12 g (30.0 mmol) of potassium carbonate, 1.89 g (10.5 mmol) of 3-(methoxycarbonyl)phenylboronic acid and 1.0 g (0.87 mmol) of tetrakis(triphenyl phosphine)palladium (0) were added, and the reaction solution was stirred at 110° C. for 10.5 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride aqueous solution in order and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=95/5-0/100 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 0.37 g of the title compound as a yellow solid (yield: 14%).

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated sodium chloride aqueous solution in order
dry with materialdried with anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-1cad897f8c3543ab892e22611a98d599
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187450B2

Reaction notes

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