Dimethylamine → HCID 59834997, compound

HRID 271261Notes

Reaction equation

HRID 271261 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.[CH3:22][NH:23][CH3:24].[CH:25](O)(C)C>O>[CH3:22][N:23]([CH3:24])[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]([O:14][CH:15]([CH3:25])[CH3:16])=[O:13])=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 3776IsopropanolHCID 86592466HCID 86592466, compound

Product 1

HCID 59834997HCID 59834997, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of ethyl 2-chloro-6-(2-furyl)-9H-purine-9-acetate (100 mg, 0.33 mol) in isopropanol (1 mL) was treated with 40% dimethylamine in water, refluxed for 2 h, cooled, poured into water, extracted with EtOAc and the combined organic phase dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; Heptane:EtOAc, (1:1)] to give the title compound (20 mg, 19%) as a white solid.

Workup

  1. temperaturerefluxed for 2 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. dry with materialthe combined organic phase dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography [SiO2; Heptane:EtOAc, (1:1)]

Sources & evidence

ORD record
ord-42c4d6c1871b406095b3d0f9883bcfe7
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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