Sodium Methoxide → 2-[(2-Cyclopropylethyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1010978Notes

Reaction equation

HRID 1010978 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][CH2:13][CH2:14][CH:15]1[CH2:17][CH2:16]1)[N:5]=2.[CH3:24][O-:25].[Na+]>CO>[CH:15]1([CH2:14][CH2:13][O:12][C:6]2[N:5]=[C:4]3[C:9]([N:10]=[C:2]([O:25][CH3:24])[N:3]3[CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:8]([NH2:11])[N:7]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 576996678-Bromo-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576996292-[(2-Cyclopropylethyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8-bromo-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.867 g) in dry MeOH (14 mL) was treated with sodium methoxide solution (3.1 mL, 25 wt. MeOH) and was heated to reflux for 5 h. The reaction was concentrated under reduced pressure before being partitioned between EtOAc (100 mL) and ammonium chloride (100 mL). The organics were separated and aqueous was re-extracted with EtOAc (100 mL). The combined organics were washed with brine (100 mL), separated and dried using a hydrophobic frit. The organics were evaporated under reduced pressure to give the title compound as a brown foam (845 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. concentrationThe reaction was concentrated under reduced pressure
  4. custombefore being partitioned between EtOAc (100 mL) and ammonium chloride (100 mL)
  5. customThe organics were separated
  6. extractionaqueous was re-extracted with EtOAc (100 mL)
  7. washThe combined organics were washed with brine (100 mL)
  8. customseparated
  9. customdried
  10. customThe organics were evaporated under reduced pressure

Sources & evidence

ORD record
ord-3fd0a6ae56f94434bebe3ceb1b1d3a34
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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