1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → {4-[2-(5-Chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-ylamino]-pyrimidin-2-yl}-carbamic acid tert-butyl ester

Participants

Reaction Steps

200 mg 4-chloro-2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridine (cf. EXAMPLE 1) and 143 mg (4-amino-pyrimidin-2-yl)-carbamic acid tert-butyl ester in 8 ml dioxane containing 444 mg Cs2CO3, 13 mg Pd2(dba)3 and 16 mg xantphos were incubated under argon gas at 80° C. for 16 hrs. After evaporation to dryness the crude sample was flashed on SiO2 with a MeOH gradient in DCM. A pooled fraction was dried down and digested with ether to give 88 mg product {4-[2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-ylamino]-pyrimidin-2-yl}-carbamic acid tert-butyl ester as a white powder with Rt˜1.80 min and correct mass found M+H˜467.

Provenance & Evidence