2-Bromoethanol → HCID 68265857, compound

Temperature

50 °C

2-(Butyloxy)-8-(methyloxy)-9-[3-(2-piperidinyl)propyl]-9H-purin-6-amine (for example, as prepared for Intermediate 12) (0.036 g, 0.10 mmol) in DMF (0.5 mL) was added to 2-bromoethanol (commercially available, for example, from Aldrich) (0.0085 mL, 0.12 mmol) (dispensed as 0.12 mL of a stock solution of 1 mmol in acetonitrile (1 mL)). 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 solution (0.080 mL, 0.08 mmol) and DIPEA (0.040 mL, 0.23 mmol) were added and heating continued for a further 18 hours. The reaction mixture was 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 4 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The residue was redissolved in methanol (0.5 mL) and applied to the top of a 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 (0.0053 g).

1. temperatureheating
2. customMeOH (0.2 mL) and the resultant solution purified by MDAP (Method A)
3. customevaporated in vacuo
4. dissolutionThe residue was dissolved in 4M HCl in dioxane (0.2 mL)
5. waitto stand at room temperature for 4 hours
6. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
7. dissolutionThe residue was redissolved in methanol (0.5 mL)
8. washThe cartridge was washed with methanol (1.5 mL)
9. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

ORD record

ord-e6d359aeb0c949b08b29d466ca5976d6

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575340B2