Sodium Methoxide → 8-(Methoxy)-2-{[2-(methyloxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-Purin-6-amine

HRID 1011025Notes

Reaction equation

Br[C:2]1[N:3]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH2:14][O:15][CH3:16])[N:5]=2.[CH3:23][O-:24].[Na+]>CO>[CH3:23][O:24][C:2]1[N:3]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH2:14][O:15][CH3:16])[N:5]=2

Participants

Conditions

Temperature: 65 °C

Procedure

8-Bromo-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.4489 g) was suspended in dry methanol (11.5 mL) and then treated with 25% (w/v) sodium methoxide in methanol (2.5 mL). The reaction mixture was heated to reflux (65° C., externally) were upon a solution was obtained. After 4 hours the reaction mixture was concentrated under reduced pressure and saturated aqueous ammonium chloride (100 mL) was added. This was then extracted with ethyl acetate (100 mL, twice). The organic layers was separated, combined and washed with brine (100 mL). The organic layer was separated and then dried by passing through a hydrophobic frit. This was then evaporated under reduced pressure to give the title compound as a white solid (1.2032 g) after placing under high vacuo, overnight.

Workup

temperatureThe reaction mixture was heated
customwas obtained
concentrationAfter 4 hours the reaction mixture was concentrated under reduced pressure and saturated aqueous ammonium chloride (100 mL)
additionwas added
extractionThis was then extracted with ethyl acetate (100 mL
customThe organic layers was separated
washwashed with brine (100 mL)
customThe organic layer was separated
customdried
customThis was then evaporated under reduced pressure

Sources & evidence

ORD record: ord-e8f772580f5c45a2b5409042f4f9f7d5
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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