Benzyl Bromide → HCID 11483653, compound

Participants

Reaction Conditions

Reaction Steps

To 2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-ylamine (100 mg, 0.46 mmol) in dry THF (10 mL), cooled to −78° C., was added LiHMDS (458 μL, 0.46 mmol). The mixture was stirred for 15 min before benzyl bromide (65 μL, 94 mg, 0.55 mmol) was added. The solution was stirred at −78° C. and allowed to warm to room temperature over a period of 16 h. Ammonium chloride solution was added (100 mL) and the product was extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried, filtered, and concentrated under vacuum. Flash column chromatography (20% EtOAc:hexane) followed by crystallisation from EtOH gave the title product as orange crystals (28 mg, 20%): mp 152-154° C. 1H-NMR (CDCl3): δ 8.07 (s, 1H, Py-H), 7.40-7.25 (m, 5H, Ph-H), 5.47 (brs, 1H, NH), 4.64 (d, 2H, J 5.8, CH2), 2.98 (m, 4H, CH2—CH2), 2.75 (s, 3H, CH3). MS (ESI+): m/z 309.11 (M+H)+. Anal. (C17H16N4S)C, H, N.

Provenance & Evidence