Tetrahydrofuran → HCID 86649314, compound

Participants

Reaction Steps

A 250 ml flask was charged with 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (2.92 g, 9.74 mmol) and 7-methyl-4-(methylthio)quinazolin-8-amine (2.00 g, 9.74 mmol) along with 20 ml of dioxane. 1.0 M LiHMDS in THF (29.2 ml, 29.2 mmol) was then added dropwise at RT. The reaction was stirred for 6 hrs and then treated with 5 ml of HOAc. The volatiles were removed under vacuum. The residue was dissolved in chloroform and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel eluting with a gradient of 20 to 60% EtOAc in hexanes to give 7-methyl-4-(methylthio)-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylquinazolin-8-amine as a yellow solid. MS Found: (ESI pos. ion) m/z 485 (M+H+).

Provenance & Evidence