Isoamyl Alcohol → 2-[(3-Methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-Purin-6-amine

HRID 1010956Notes

Reaction equation

[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][OH:5].CC(C)([O-])C.[Na+].Cl[C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH2:29])[N:15]=1>COCCOC.O>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][O:5][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH2:29])[N:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To 3-methyl-1-butanol (1.03 mL) in DME (5 mL) was added sodium tert-butoxide (912 mg) in portions over 5 mins with stirring. The mixture was stirred at room temperature until homogeneous. 2-Chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (600 mg) was added followed by DME (4.6 mL). The reaction was heated at 110° C. overnight. The reaction was allowed to cool, was taken up in water (20 mL) and washed with EtOAc (2×20 mL). The organics were extracted with brine, separated, dried over MgSO4, filtered 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 (30-80%) to afford the title compound as a yellow residue (266 mg).

Workup

stirringThe mixture was stirred at room temperature until homogeneous
temperatureto cool
washwashed with EtOAc (2×20 mL)
extractionThe organics were extracted with brine
customseparated
dry with materialdried over MgSO4
filtrationfiltered
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-e42910d434ed4ce9a9be54f31f6736d6
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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