Potassium Carbonate → 2-[(2-cyclopropylethyl)oxy]-8-(methyloxy)-9-[2-(tetrahydro-3-furanyl)ethyl]-9H-purin-6-amine

HRID 1011107Notes

Reaction equation

FC(F)(F)C(O)=O.[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[NH:15][C:16]([NH2:25])=[C:17]3[C:21]([N:22]=2)=[N:20][C:19]([O:23][CH3:24])=[N:18]3)[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH:35]1[CH2:39][CH2:38][O:37][CH2:36]1>CN(C=O)C>[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([O:23][CH3:24])[N:20]3[CH2:33][CH2:34][CH:35]3[CH2:39][CH2:38][O:37][CH2:36]3)=[C:16]([NH2:25])[N:15]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-[(2-cyclopropylethyl)oxy]-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (0.16 g, 0.450 mmol) and anhydrous potassium carbonate (0.243 g, 1.762 mmol) in DMF (2.5 ml) was heated at 50° C. for 1 hour. The mixture was cooled to room temperature and 3-(2-bromoethyl)tetrahydrofuran (0.095 g, 0.528 mmol) was added and the mixture heated at 50° C. for 18 hours. The mixture was quenched with water (2 ml) and extracted with DCM (2×5 ml). The DCM was separated through a hydrophobic frit and evaporated by blowing down under a stream of nitrogen. The sample was dissolved in 1:1 MeOH:DMSO (3×0.5 ml) and purified by mass directed autopreparation. Product containing fractions were evaporated under a stream of nitrogen in a blowdown apparatus to give the title compound as a white solid (98 mg).

Workup

temperatureThe mixture was cooled to room temperature
temperaturethe mixture heated at 50° C. for 18 hours
customThe mixture was quenched with water (2 ml)
extractionextracted with DCM (2×5 ml)
customThe DCM was separated through a hydrophobic frit
customevaporated
dissolutionThe sample was dissolved in 1:1 MeOH
customDMSO (3×0.5 ml) and purified by mass
additionProduct containing fractions
customwere evaporated under a stream of nitrogen in a blowdown apparatus

Sources & evidence

ORD record: ord-ae6cf48489c8472aa1a058d9a4d53424
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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