Methoxymethyl-triphenylphosphonium chloride → HCID 86618379, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methoxymethyl triphenylphosphonium chloride (7.24 g) in THF (100 mL) at 0° C. was added n-butyllithium (6.76 mL of a 2.M solution in hexanes). The reaction mixture was stirred at 0° C. for 1 h and then a suspension of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 (2 g) in THF (30 mL) was added dropwise. The reaction mixture was stirred at room temperature for 16 h and then quenched with water (80 mL) and extracted with ethyl acetate (2×80 mL). The combined organics were washed with aqueous brine solution (2×80 mL), dried (MgSO4), concentrated and purified using column chromatography to give 2-chloro-6-(2-methoxy-vinyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (mixture of cis/trans isomers) as a yellow solid (2.24 g).

Provenance & Evidence