Sodium Methoxide → 2-[(1-Methylethyl)oxy]-8-(methyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1616294Notes

Reaction equation

Br[C:2]1[N:3]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH:13]([CH3:15])[CH3:14])[N:5]=2.[CH3:22][O-:23].[Na+]>CO>[CH3:14][CH:13]([O:12][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([O:23][CH3:22])[N:3]2[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[C:8]([NH2:11])[N:7]=1)[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of 8-bromo-2-[(1-methylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (690 mg, 1.937 mmol) in methanol (15 ml) was added sodium methoxide (30% wt/v solution in methanol, 2.4 ml) and the reaction mixture heated at 50° C. for 2 hours. The reaction mixture was then heated to 70° C. and stirred for 2.5 hours. The solvent was evaporated and the residue partioned between saturated aqueous ammonium chloride solution (15 ml) and ethyl acetate (20 mL). The layers were separated, the aqueous phase was extracted with additional ethyl acetate (2×10 mL) and the organic extracts were combined, dried by passage through a hydrophobic frit and evaporated to give the title compound as a yellow solid (573 mg).

Workup

temperatureThe reaction mixture was then heated to 70° C.
customThe solvent was evaporated
customThe layers were separated
extractionthe aqueous phase was extracted with additional ethyl acetate (2×10 mL)
customdried by passage through a hydrophobic frit
customevaporated

Sources & evidence

ORD record: ord-53d1baecf5a241a2823d81c7fe81831f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765772B2

Reaction notes

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