Acrylonitrile → (+/-)-trans-3-{[3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexyl]-oxy}propanenitrile

Participants

Reaction Steps

Add a solution of approx. 2 mg of potassium tert-butoxide in 0.2 ml of THF dropwise to a solution of 34.4 mg (0.059 mmol) of (+/−)-trans-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol in 0.23 ml of acrylonitrile. Stir the reaction mixture with exclusion of light at RT for approx. 2 h. After diluting with dichloromethane, wash successively with 1N hydrochloric acid, satd. sodium hydrogencarbonate solution and satd. sodium chloride solution, and concentrate the organic phase under reduced pressure. After the residue has been purified by means of preparative RP-HPLC (eluent: acetonitrile/water gradient), 33.6 mg of the target product are obtained (86.6% of theory).

Provenance & Evidence