Potassium Carbonate → 2-[(1-Methylbutyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

HRID 1010971Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-[(1-methylbutyl)oxy]-8-methoxy-9H-purin-6-amine trifluoroacetic acid salt (218 mg) in dry DMF (3.71 mL) was added potassium carbonate (330 mg). The mixture was stirred at 60° C. for 90 mins. The reaction was cooled and 4-(bromomethyl)tetrahydro-2H-pyran (118 mg) was added. The reaction was stirred at 50° C. for 6 h and was cooled to room temperature. The mixture was taken up in EtOAc (40 mL) and washed with water (2×20 mL). The organics were separated, dried over MgSO4 and concentrated in vacuo to give a viscous yellow oil. The 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 oil (92 mg).

Workup

temperatureThe reaction was cooled
stirringThe reaction was stirred at 50° C. for 6 h
temperaturewas cooled to room temperature
washwashed with water (2×20 mL)
customThe organics were separated
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give a viscous yellow oil
customThe material was purified by C18 reverse phase chromatography (ISCO)

Sources & evidence

ORD record: ord-134f8d1998c148abae526de33ef882f2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

Loading…