Sodium Methoxide → HCID 59835072, compound

HRID 271263Notes

Reaction equation

HRID 271263 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1.[CH3:24][O-:25].[Na+]>CO>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:4]1[N:3]=[C:2]([O:25][CH3:24])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59835019HCID 59835019, compound

Product 1

HCID 59835072HCID 59835072, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-6-(2-furyl)-9-(2-trimethylsilylethoxymethyl)-9H-purine (0.35 g, 1.0 mmol) and sodium methoxide (60 mg, 1.1 mmol) in methanol (5 mL) was refluxed for 23 h, cooled, concentrated in vacuo and the resulting solid treated with water, acidified to pH 4 with acetic acid, extracted with EtOAc, dried (Na2SO4), concentrated in vacuo and purified by chromatography [SiO2; EtOAc:heptane (1:1)]to give the title compound (232 mg, 67%) as a pale yellow solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionthe resulting solid treated with water
  4. extractionextracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography [SiO2

Sources & evidence

ORD record
ord-d68d3f63ad8f4c05b013c4b9098f93a4
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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