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

HRID 527808Notes

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-b1ff85a45829445292ac3d17fc370495
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346806B2

Reaction notes

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