Lithium Hexamethyldisilazide → HCID 9907029, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-chloro-3-(5-methylisoxazol-3-yl)-1,2,3a,4,6-pentaaza-cyclopenta[a]naphthalene (100 mg, 0.35 mmol) in N,N-dimethyl formamide (7 ml) was added to a solution of 2-methyl-1,2,4-triazole-3-methanol (43 mg, 0.38 mmol) (prepared using the conditions of Itoh and Okongi, EP-A-421210) under nitrogen, and the mixture cooled to −78° C. Lithium bis(trimethylsilyl)amide (0.42 ml, 1.0 M in tetrahydrofuran, 0.42 mmol) was added, and the reaction stirred at −78° C. for 2 h, then allowed to warm to room temperature and stirred for 3 h. The solvents were evaporated by azeotroping with xylene and the residue pre-absorbed onto silica (1 g) from methanol/dichloromethane. Flash chromatography on a silica bond elute cartridge (10 g) eluting with a 0%→5% methanol/dichloromethane gradient, followed by recrystallisation (dichloromethane/ethyl acetate) gave the title-product (52 mg, 41%), mp 255-257° C.; 1H NMR (360 MHz, CDCl3) δ 9.16 (1H, dd, J=4.4 Hz and 1.7 Hz, Ar—H), 9.01 (1H, dd, J=8.2 Hz and 1.7 Hz, Ar—H), 7.92 (1H, m, Ar—H), 7.90 (1H, s, Ar—H), 6.93 (1H, s, Ar—H), 5.88 (2H, s, CH2), 4.12 (3H, s, CH3), 2.60 (3H, s, CH3); MS (ES+) m/e 364 [MH]+.

Provenance & Evidence