18-Crown-6 → 4-(2-((Quinazolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

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Reaction Steps

To a solution of compound 1d (600.0 mg, 2.50 mmol) in THF (10 mL) was added 18-crown-6 (677 mg, 2.60 mmol), followed by potassium tert-butoxide (575 mg, 5.12 mmol). The reaction mixture was stirred at rt for 10 min and treated with 2-chloroquinazoline (632 mg, 3.84 mmol). The resulting mixture was stirred for 10 more min at rt and then at 120° C. for 1 h. The reaction mixture was then allowed to cool to rt, diluted with 20 mL of DCM and 20 mL of saturated aqueous NH4Cl. The organic layer was separated, dried over Na2SO4, and concentrated. The residue obtained was purified by flash column chromatography on silica gel (1:0-4:1 DCM/EtOAc) to obtain a white solid. The solid was then suspended in diethyl ether (50 mL) and sonicated for 5 min, before collecting by filtration to yield compound 22a. Mass Spectrum (LCMS, ESI pos.) Calcd. For C19H18N6O2: 363.1 (M+H). Found 363.1.

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