Cyclopropylacetylene → HCID 86665091, compound

Participants

Reaction Steps

To a flask was added 2,4-dichlorofuro[3,2-d]pyrimidine (0.30 g, 1.6 mmol, ArkPharm), PPh3 (0.008 g, 0.03 mmol) in THF (1.2 mL) and TEA (1.764 mL). The mixture was placed under vacuum and purged with N2 three times, then Pd(PPh3)2Cl2 (0.011 g, 0.016 mmol) and CuI (0.006 g, 0.03 mmol) were added. The mixture was placed under vacuum and purged with N2 three times and then ethynylcyclopropane (0.161 mL, 1.905 mmol) was added. The mixture was placed under vacuum and purged with N2 and then the mixture was stirred at rt for about 18 h. The mixture was filtered and the filter cake was washed with EtOAc (3×20 mL). The filtrate was concentrated under reduced pressure and the residue was deposited on silica gel and purified by column chromatography (12 g silica gel, 0 to 30% EtOAc/heptane) to give 2-chloro-4-(cyclopropylethynyl)furo[3,2-d]pyrimidine (0.090 g, 26%): LC/MS (Table 2, Method c) Rt=2.11 min; MS m/z 219 (M+H)+.

Provenance & Evidence