1-Iodopropane → Methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)pentanoate

Temperature

-15 °C

A solution of methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)acetate (150 mg; 0.471 mmol) in dry DMF (2.5 mL) was cooled to −15° C. LHMDS (0.518 mL; 0.518 mmol; 1M in THF) was added dropwise and the mixture was stirred at −15° C. for 15 min followed by the dropwise addition of iodopropane (0.069 mL; 0.707 mmol), after stirring for 2 h at −15° C. the mixture was allowed to warm to room temperature. After 1 h the reaction was quenched by adding a saturated solution of ammonium chloride. The mixture was extracted twice with ethyl acetate and the combined organic layers were washed with brine and 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 (1-10%) in heptane to give 94 mg (54%) of the title compound as a colorless oil. ESI/APCI(+): 361 (M+H).

1. stirringafter stirring for 2 h at −15° C. the mixture
2. temperatureto warm to room temperature
3. customAfter 1 h the reaction was quenched
4. additionby adding a saturated solution of ammonium chloride
5. extractionThe mixture was extracted twice with ethyl acetate
6. washthe combined organic layers were washed with brine
7. dry with materialdried over magnesium sulphate
8. concentrationconcentrated under reduced pressure
9. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (1-10%) in heptane

ORD record

ord-6577dffaa6604e5fa795b1f14b3b9ce6

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906906B2