1,4-Dioxane → 6-Amino-2-{[(1R)-1-methylbutyl]oxy}-9-[2-(tetrahydro-2-furanyl)ethyl]-7,9-dihydro-8H-Purin-8-one

HRID 1011210Notes

Reaction equation

[CH3:1][C@@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:23]C)[N:13]2[CH2:16][CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][O:19]2)=[C:9]([NH2:25])[N:8]=1)[CH2:3][CH2:4][CH3:5].O1CCOCC1>CO>[NH2:25][C:9]1[N:8]=[C:7]([O:6][C@H:2]([CH3:1])[CH2:3][CH2:4][CH3:5])[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:23])[N:13]2[CH2:16][CH2:17][CH:18]1[CH2:22][CH2:21][CH2:20][O:19]1

Participants

Conditions

Temperature: 37 °C

Procedure

To a solution of 2-{[(1R)-1-methylbutyl]oxy}-8-(methyloxy)-9-[2-(tetrahydro-2-furanyl)ethyl]-9H-purin-6-amine (50 mg, 0.143 mmol) in methanol (10 ml) at room temperature was added 4M HCL in 1,4 dioxane (0.894 ml, 3.58 mmol) to give a pale straw coloured solution. The reaction mixture was stirred at 37° C. for 3 hours, and the solvent removed on a nitrogen blowdown unit overnight. The residue was dissolved in methanol and loaded onto a 2 g aminopropyl SPE cartridge and eluted with methanol. The appropriate fractions were combined and dried under a stream of nitrogen in a blowdown apparatus to give the title compound as a white solid (26 mg).

Workup

customto give a pale straw coloured solution
customthe solvent removed on a nitrogen blowdown unit overnight
dissolutionThe residue was dissolved in methanol
washeluted with methanol
customdried under a stream of nitrogen in a blowdown apparatus

Sources & evidence

ORD record: ord-5c2b00a6895b406a9b9915a0061788e1
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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