Dimethyl Sulfoxide → 6-Amino-2-(butyloxy)-9-[2-(1-butyl-4-piperidinyl)ethyl]-7,9-dihydro-8H-purin-8-one

Participants

Reaction Conditions

Reaction Steps

1-Iodobutane (0.1 mmol) was weighed into a tube and an aliquot (0.4 ml, 0.12 mmol) of a solution of 2-(butyloxy)-8-(methyloxy)-9-[2-(4-piperidinyl)ethyl]-9H-purin-6-amine (0.418 g mg, 1.2 mmol) suspended in DMF (4.8 ml) was added. DIPEA (40 μl, 0.229 mmol) was added and the tube was heated at 50° C. for 18 hours. An additional portion of 1-iodobutane (15 μl) and DIPEA (20 μl) was added and heating continued for a further 18 hours. DMSO (200 uL) was added and the mixture purified by Mass Directed AutoPrep (Method A). The solvent was evaporated in vacuo using the Genevac. The residue was redissolved in 4M HCl/dioxane (0.2 ml), capped and stood at room temperature for 18 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The sample was dissolved in 1:1 DMSO:MeOH and purified by MDAP (Method C) and the solvent was evaporated in vacuo using the Genevac. The material was redissolved in methanol (0.5 ml), and applied to a 0.1 g aminopropyl SPE (preconditioned with methanol, 1.5 ml). The cartridge was eluted with methanol (1.5 ml), the solvent was removed to give the title compound (4.8 mg).

Provenance & Evidence