2-Bromoethanol → HCID 53355058, compound

Participants

Reaction Conditions

Reaction Steps

2-(Butyloxy)-8-(methyloxy)-9-[4-(4-piperidinyl)butyl]-9H-purin-6-amine (for example, as prepared for Intermediate 34) (0.038 g, 0.10 mmol) in DMF (0.4 mL) was added to 2-bromoethanol (0.0085 mL, 0.12 mmol). DIPEA (0.040 mL, 0.23 mmol) was added and the reaction mixture heated at 50° C. for 18 hours. An additional aliquot of the 2-bromoethanol (commercially available, for example, from Aldrich) (0.015 mL) and DIPEA (0.040 mL, 0.23 mmol) were added and heating continued for a further 7 hours. The reaction mixture were stirred at room temperature for 72 hours then diluted with DMSO:MeOH (0.2 mL) and the resultant solution purified by MDAP (Method A). Appropriate fractions were combined and evaporated in vacuo. The residue was dissolved in 4M HCl in dioxane (0.2 mL) and allowed to stand at room temperature for 18 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The samples were dissolved in 1:1 MeOH:DMSO (0.6 mL) and purified by Mass Directed AutoPrep on Sunfire C18 column using Acetonitrile Water with a TFA modifier. The solvent was evaporated in vacuo. The residue was redissolved in methanol (0.5 mL) and applied to top of 0.1 g aminopropyl SPE (preconditioned with methanol, 1.5 mL). The cartridge was washed with methanol (1.5 mL). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the title compound (0.0133 g).

Provenance & Evidence