Purine, 6-bromo- → HCID 178527266, compound

HRID 735337Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([O-:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[Na+].Br[C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[NH:25][CH:26]=[N:27]2>CS(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:23]2[N:31]=[CH:30][N:29]=[C:28]4[C:24]=2[N:25]=[CH:26][NH:27]4)(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate [prepared according to the method of Example 10(a) Steps 1-2] (104 mg, 0.34 mmol) and 6-bromopurine (70 mg, 0.35 mmol) in dimethylsulfoxide (4 mL) was stirred at 80° C. (oil bath temperature) under nitrogen for 22 hours. The cooled reaction mixture was diluted with water (20 mL), the preciptate formed collected under suction, washed with water and dried in vacuo. Purification by flash chromatography, eluting with 5% methanol in dichloromethane, gave the title compound as a white solid (33 mg, 25%). 1H NMR (500 MHz, DMSO-d6) δ 14.06 (1H, br s), 9.04 (1H, s), 8.92 (1H, s), 8.86 (1H, s), 8.38 (1H, s), 8.35 (1H, d, J 8.7 Hz), 8.23 (1H, d, J 8.7 Hz), 8.05 (2H, m), 7.92 (2H, m), 7.38 (2H, m); m/z (ES+) 405 [MH+].

Workup

customprepared
customThe cooled reaction mixture
customthe preciptate formed
customcollected under suction
washwashed with water
customdried in vacuo
customPurification by flash chromatography
washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-343e16caf8be44a596a63e5451d0eb30
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592456B2

Reaction notes

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