Lithium Hexamethyldisilazide → 4-(2,3-Dichlorobenzyl)-2-(methylthio)thiazolo[4,5-d]pyrimidin-7(4H)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-(methylthio)thiazolo[4,5-d]pyrimidin-7(4H)-one (2.978 g, 14.94 mmol) in THF (200 mL) at 0° C. was added dropwise of LiHMDS (18.3 mL, 16.44 mmol). The resulting mixture was stirred at 0-5° C. for 3 hours and 1-(bromomethyl)-2,3-dichlorobenzene (3.946 g, 16.44 mmol) in THF (30 mL) was added dropwise to the reaction mixture over a period of 2 hours. The reaction mixture was allowed to warm to ambient temperature slowly and stirred at ambient temperature for 16 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (2×20 cm, DCM:MeOH=30:1 elution) to give the desired product as a white solid (0.671 g, 13%). 1H NMR (300 MHz, CDCl3) δ 8.33 (s, 1H), 7.50 (m, 1H), 7.26˜7.16 (m, 2H), 5.56 (s, 2H), 2.74 (s, 3H); LC-MS: 358 (MH+); IR (thin film): 3073, 2986, 1651, 1619, 1598, 1426, 1384, 1221, 1055 cm−1.

Provenance & Evidence