Lithium Hexamethyldisilazide → HCID 66780392, compound

Participants

Reaction Steps

A solution of 5-methyl-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (75 mg, 0.297 mmol) in Tetrahydrofuran (THF) (1.5 mL) was stirred at 0° C. for 15 min, then lithium bis(trimethylsilyl)amide (446 μl, 0.446 mmol, 1.0 M in THF) was added and stirring was continued for 30 min. 2,3-Dichlorobenzyl bromide (86 mg, 0.357 mmol) was added and the mixture was allowed to warm to room temperature and stirred overnight. Additional stirring at 65° C. for 2 h completed the reaction resulting in a mixture of the desired product and the regio-isomer. The reaction was concentrated and the residue was purified by reversed-phase HPLC to provide the product, 4-[(2,3-dichlorophenyl)methyl]-5-methyl-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (28 mg, 23%). LC/MS: MS (ES+) m/e 411 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.44 (s, 3H) 3.52 (m, 4H) 3.64-3.72 (m, 4H) 5.60 (s, 2H) 6.90 (d, J=7.3 Hz, 1H) 7.33 (m, 1H) 7.64 (d, J=8.0 Hz, 1H).

Provenance & Evidence