1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 2-(4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

A 100 mL flask was charged with 4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.78 g, 16 mmol), 2-bromo-5-methylbenzonitrile (4.18 g, 19.2 mmol), bis(dibenzylideneacetone)palladium(0) (372 mg, 0.64 mmol), xantphos (529 mg, 0.896 mmol), and sodium tert-butoxide (2.33 g, 24 mmol), capped with a septum and purged with nitrogen. Dry argon-sparged toluene (50 mL) was added. The heterogeneous mixture was placed in an oil bath at 100° C., and heated under argon overnight. After 14 hours, TLC showed the reaction was complete. The mixture was removed from the heat, diluted with ethyl acetate (50 mL), filtered and concentrated in vacuo. The residue was purified by silica gel column (0-100% EtOAc/hexane) to afford a light orange solid.

1. customcapped with a septum
2. custompurged with nitrogen
3. customDry argon-sparged toluene (50 mL)
4. additionwas added
5. customThe heterogeneous mixture was placed in an oil bath at 100° C.
6. temperatureheated under argon overnight
7. customThe mixture was removed from the heat
8. additiondiluted with ethyl acetate (50 mL)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by silica gel column (0-100% EtOAc/hexane)
12. customto afford a light orange solid

ORD 기록

ord-21cd55d605a647a0bbd887eacb573e8f

출처 데이터셋

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08076345B2