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

HRID 1010950Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][C:9]([CH3:27])([CH2:24][CH2:25][CH3:26])[CH2:10][O:11][C:12]1[N:20]=[C:19]2[C:15]([N:16]=[C:17]([O:21][CH3:22])[NH:18]2)=[C:14]([NH2:23])[N:13]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CN(C=O)C.CCOC(C)=O>[CH3:8][C:9]([CH3:27])([CH2:24][CH2:25][CH3:26])[CH2:10][O:11][C:12]1[N:20]=[C:19]2[C:15]([N:16]=[C:17]([O:21][CH3:22])[N:18]2[CH2:35][CH:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:14]([NH2:23])[N:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-[(2,2-dimethylpentyl)oxy]-8-methoxy-9H-purin-6-amine trifluoroacetic acid salt (252 mg) in dry DMF (3.97 mL) was added potassium carbonate (356 mg). The mixture was stirred at 60° C. for 90 mins. The reaction was cooled and 4-(bromomethyl)tetrahydro-2H-pyran (127 mg) was added. The mixture was stirred at 50° C. for 6 h. The reaction was cooled and taken up in EtOAc (40 mL). The mixture was washed with water (2×20 mL) and the organics were separated, dried over MgSO4 and concentrated in vacuo to give a viscous 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 (30-80%) to afford the title compound as an off-white solid (116 mg).

Workup

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

Sources & evidence

ORD record: ord-0d42eaa78544492fa7fca053bbebea76
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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