Hexane → HCID 86584210, compound

Participants

Reaction Steps

To 2,6-dichloropurine (8.86 g, 57.73 mmol) dissolved in a mixture of CH2Cl2 (200 mL), MeOH (50 mL) and DPEA (7.71 mL, 63.50 mmol) was added N1-(trimethylsilylethoxycarbonyl) piperazine (13.30 g, 57.73 mmol) as a solid. The reaction progress was monitored by thin layer chromatography MeOH:EtOAc:hexane (1/49/50, v/v/v) which showed disappearance of starting material and formation of a new product spot after 15 hours. The solvent was removed in vacuo and the residue left behind was partitioned between water (100 mL) and CH2Cl2 (100 mL). The water layer was separated and extracted twice with CH2Cl2 (50 mL). The CH2Cl2 fractions were combined and washed with brine (100 mL), dried (MgSO4), filtered and evaporated. The residue was purified by silica gel flash column chromatography using MeOH:EtOAc:CH2Cl2 (1/49/50, v/v/v) as the eluent. The appropriate fractions were pooled and evaporated to give 15.70 g (71%) of the title compound. 1H NMR (CDCl3): δ 0.02 (s, 9H), 1.04 (t, 2H), 3.69 (t, 4H), 4.25 (t, 2H), 4.40 (bs, 4AH), 7.99 (s, 1H), 13.5 (bs, NH).

Provenance & Evidence