Compound 10
6,6′-((1R,2R,3S,4S)-2,4-diphenylcyclobutane-1,3-diyl)bis(2-chloropyrimidine)
From: Inhibiting androgen receptor nuclear entry in castration-resistant prostate cancer
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
23 (179 mg, 1 mmol) was crushed between two borosilicate plates. The plate was placed about ½-1 inch below a water-cooled 450 W low pressure mercury immersion lamp and then irradiated for 1 h. The material was isolated and did not require any purification to yield 176 mg (98 % yield) of light yellow solid CB10. 1H NMR (499 MHz, CDCl3) δ 8.26 (d, J = 5.1 Hz, 2H), 7.26 – 7.08 (m, 10H), 6.87 (d, J = 5.1 Hz, 2H), 4.90 (dd, J = 10.3, 7.3 Hz, 2H), 4.67 (dd, J = 10.3, 7.2 Hz, 2H). 13C NMR (126 MHz, CDCl3) δ 171.7, 161.1, 158.5, 137.9, 128.4, 127.8, 127.0, 119.2, 47.7, 44.8. HRMS (ESI+) m/z calcd for C24H19N4Cl2+ 433.0987, found 433.0985.
