Dimethylformamide → HCID 88852845, compound

Participants

Reaction Conditions

Reaction Steps

9-(3-(isopropylamino)propyl)-8-(6-(oxazol-2-yl)benzo[d][1,3]dioxol-5-ylthio)-9H-purin-6-amine [DZ4-20]. A mixture of PU-H71 (30 mg, 0.0585 mmol), 2-(tri-n-butylstannyl)oxazole (83.8 mg, 49 μl, 0.234 mmol), LiCl (5 mg, 0.117 mmol) and Pd(PPh3)4 (6.7 mg, 0.0058 mmol) in DMF (1 mL) was evacuated and back filled with nitrogen. This was repeated four times then the reaction mixture was heated under nitrogen at 90° C. for 18 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAC:MeOH—NH3 (7N), 2:2:1:0.5) to give 20.8 mg (78%) of DZ4-20. 1H NMR (500 MHz, CDCl3/MeOH-d4) δ 8.25 (s, 1H), 7.75 (s, 1H), 7.46 (s, 1H), 7.27 (s, 1H), 6.71 (s, 1H), 6.06 (s, 2H), 4.26 (t, J=6.9 Hz, 2H), 2.75 (septet, J=6.3 Hz, 1H), 2.53 (t, J=6.9 Hz, 2H), 1.98 (m, 2H), 1.06 (d, J=6.3 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C21H24N7O3S, 454.1661; found. 454.1650; HPLC: method A Rt=5.77, method B Rt=5.28.

Provenance & Evidence