(+/-)-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

HRID 2189046Notes

Reaction equation

HRID 2189046 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH:21]([OH:25])[CH2:20]4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:5][CH:4]=1>O.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][C@H:19]4[CH2:24][CH2:23][CH2:22][C@H:21]([OH:25])[CH2:20]4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:7][CH:8]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][C@@H:19]4[CH2:24][CH2:23][CH2:22][C@H:21]([OH:25])[CH2:20]4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 58280156(+/-)-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol

Product 2

HCID 58280259trans-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanolYield 14.3%HCID 86653753(+/-)-cis-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanolYield 50%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

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.

Sources & evidence

ORD record
ord-8a42e216389d4e20865c188a93e9bf02
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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