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

HRID 1011074Notes

Reaction equation

HRID 1011074 reaction equation
Br[C:2]1[N:3]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][C@H:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[N:5]=2.[CH3:24][O-:25].[Na+]>CO>[CH3:17][C@@H:13]([O:12][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([O:25][CH3:24])[N:3]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[C:8]([NH2:11])[N:7]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 576998388-Bromo-2-{[(1R)-1-methylbutyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576995882-{[(1R)-1-Methylbutyl]oxy}-8-(methyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

8-bromo-2-{[(1R)-1-methylbutyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (5.23 g, 13.61 mmol) was heated to reflux with 25% sodium methoxide in methanol (8.8 ml, 13.61 mmol) and methanol (40 ml) for 4 hours. The reaction mixture was concentrated under reduced pressure and partitioned between saturated ammonium chloride (100 ml) and dichloromethane (100 ml). The aqueous was washed with further dichloromethane (100 ml) and the combined organics passed through a hydrophobic frit and concentrated to give the title compound as a pale yellow foam (4.80 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between saturated ammonium chloride (100 ml) and dichloromethane (100 ml)
  3. washThe aqueous was washed with further dichloromethane (100 ml)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c01ec4602ef946d5ae6d4a6a7abe779e
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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