1-Chloro-2-iodoethane → 5-(2-Ethylbenzoimidazol-1-yl)-2-iodo-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of 5 -(2-ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine (1.92 g, 5.23 mmol) in THF (60 mL) was cooled to −40° C. before the drop wise addition of LiHMDS (6.3 mL, 6.28 mmol, 1 M solution in THF). The resulting mixture was warmed to −5° C. over 30 min then mixture was cooled back to −30° C. before the addition of a solution of 1-chloro-2-iodoethane (2.0 g, 10.47 mmol) in THF (6 mL) The resulting mixture was allowed to warm to 0° C. then quenched with NH4Cl and extracted with EtOAc. The combined organics were washed with brine then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 50-80%) followed by recrystallisation from iPrOAc affording the title compound as a yellow solid (1.58 g, 62%)._LCMS (method A): RT 3.50 min [M+H]+ 493.0

Provenance & Evidence