Purine → HCID 89544202, compound

To a mixture of purine (0.24 g, 2.0 mmol), copper(II) acetate (0.36 g, 2.0 mmol) and N,N,N′,N′-tetramethylethylenediamine (0.6 mL, 4 mmol) in a mixture of methanol (160 mL) and water (40 mL) was added (5-chloro-2-hydroxyphenyl)boronic acid (0.69 g, 4.0 mmol). The reaction mixture was stirred vigorously open to the atmosphere at ambient temperature for 2 h. The mixture was filtered over a pad of diatomaceous earth and the pad was washed with a mixture of dichloromethane (50 mL) and methanol (50 mL). The filtrate was concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-10% gradient of methanol in dichloromethane, followed by trituration in a mixture of ethyl acetate and hexanes, to afford 4-chloro-2-(9H-purin-9-yl)phenol as a tan solid in 20% yield (0.098 g): 1H NMR (300 MHz, DMSO-d6) δ10.65 (s, 1H), 9.26 (s, 1H), 8.95 (s, 1H), 8.76 (s, 1H), 7.73-7.67 (m, 1H), 7.49-7.41 (m, 1H), 7.17-7.09 (m, 1H); MS (ES+) m/z 247.0 (M+1), 248.9 (M+1).

1. filtrationThe mixture was filtered over a pad of diatomaceous earth
2. washthe pad was washed with a mixture of dichloromethane (50 mL) and methanol (50 mL)
3. concentrationThe filtrate was concentrated in vacuo
4. customThe residue was purified by column chromatography
5. washeluting with a 0-10% gradient of methanol in dichloromethane
6. additionfollowed by trituration in a mixture of ethyl acetate and hexanes

ORD record

ord-0c403b030ad7474cae80027171a96a15

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365578B2