Potassium Carbonate → 2-[(3-Methylbutyl)oxy]-8-(methoxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

HRID 1010960

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-[(3-methylbutyl)oxy]-8-methoxy-9H-purin-6-amine trifluoroacetic acid salt (143 mg) in dry DMF (2.42 mL) was added potassium carbonate (217 mg) and the mixture was stirred at 60° C. for 90 mins. The reaction was cooled and 4-(bromomethyl)tetrahydro-2H-pyran (77 mg) was added. The reaction was stirred at 50° C. overnight and was cooled to room temperature. The mixture was taken up in EtOAc (30 mL) and extracted with water (2×15 mL). The organics were separated, dried over MgSO4 and concentrated in vacuo to give a viscous yellow oil. The crude material was purified by C18 reverse phase chromatography (ISCO) using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-60%) to afford the title compound as a clear viscous oil (52 mg).

Workup

temperatureThe reaction was cooled
stirringThe reaction was stirred at 50° C. overnight
temperaturewas cooled to room temperature
extractionextracted with water (2×15 mL)
customThe organics were separated
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give a viscous yellow oil
customThe crude material was purified by C18 reverse phase chromatography (ISCO)

Sources & evidence

ORD record: ord-cf5cfc4829a84a3ab98772b553ea6811
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Linked notes

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