(+/-)-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol → (+/-)-cis-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol

Participants

Reaction Steps

Separate 300 mg (0.72 mmol) of (+/−)-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol (cis/trans mixture) by preparative HPLC into the pure cis- and trans isomers [column: Phenomenex Gemini, C-18, 5 μm, 250 mm×21.2 mm; flow rate: 20 ml/min; temperature: 25° C.; eluent: water/THF 60:40]. 43 mg (14.3% of theory) of (+/−)-trans-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol (Example 58A) and 150 mg (50.0% of theory) of (+/−)-cis-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol (Example 59A) are obtained.

Provenance & Evidence