Phenylboronic Acid → Methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)acetate

Methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)acetate (200 mg; 0.723 mmol), benzeneboronic acid (264 mg; 2.168 mmol), tetrakis(triphenylphosphine) palladium(0) (84 mg; 0.072 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (3 mL) and water (1 mL). N,N-Diisopropylethylamine (0.444 mL; 2.89 mmol) was added, the tube was sealed and irradiated in a microwave oven at 130° C. for 1 h. The reaction mixture was partitioned between brine and ethyl acetate, the phases were separated and the water layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane to give 212 mg (91%) of methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)acetate as a white solid. ESI/APCI(+): 319 (M+H).

1. customthe tube was sealed
2. customirradiated in a microwave oven at 130° C. for 1 h
3. customThe reaction mixture was partitioned between brine and ethyl acetate
4. customthe phases were separated
5. extractionthe water layer was extracted with ethyl acetate
6. dry with materialThe combined organic layers were dried over magnesium sulphate
7. concentrationconcentrated under reduced pressure
8. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane

ORD-Eintrag

ord-42bd64f7225a4e37918f802b73120364

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08906906B2