Potassium Phosphate, Tribasic → HCID 59562421, compound

HRID 1849976Notes

Reaction equation

Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:3]=1.[CH3:16][C:17]1([CH3:27])[C:22](=[O:23])[CH2:21][C:20](=[O:24])[C:19]([CH3:26])([CH3:25])[O:18]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2[N:3]=[C:2]([CH:21]3[C:20](=[O:24])[C:19]([CH3:25])([CH3:26])[O:18][C:17]([CH3:27])([CH3:16])[C:22]3=[O:23])[C:7]([CH3:8])=[CH:6][N:5]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave vial is charged with 4-chloro-2-(4-chlorophenyl)-5-methylpyrimidine (239 mg, 1 mmol), 2,2,6,6-tetramethyl-pyran-3,5-dione (170 mg, 1 mmol), palladium acetate (12 mg, 0.05 mmol), X-Phos (48 mg, 0.1 mmol) and potassium phosphate (424 mg, 2 mmol). 1,2-dimethoxyethane (3 ml) is added and the reaction heated to 150° C., with stirring, for 30 minutes. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-[2-(4-chlorophenyl)-5-methylpyrimidin-4-yl]-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

additionSilica gel is added to the crude
customreaction mixture
customthe solvent is evaporated under reduced pressure
customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-d038ff2db8dc484aba7474259e118432
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956999B2

Reaction notes

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