Methyl iodide → HCID 14100209, compound

HRID 621490Notes

Reaction equation

HRID 621490 reaction equation
[CH2:1]([N:8]1[C:13]2[NH:14][N:15]=[C:16]([NH:17][CH3:18])[C:12]=2[C:11](=[O:19])[N:10]([CH2:20][CH2:21][CH2:22][CH3:23])[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:27](=O)([O-])[O-].[K+].[K+]>>[CH2:1]([N:8]1[C:13]2=[N:14][N:15]([CH3:27])[C:16]([NH:17][CH3:18])=[C:12]2[C:11](=[O:19])[N:10]([CH2:20][CH2:21][CH2:22][CH3:23])[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178448663HCID 178448663, compound

Product 1

HCID 14100209HCID 14100209, compoundYield 56.3%

Procedure

A mixture of 7-benzyl-5-butyl-3-methylaminopyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (1.5 g, 4.58 mM), methyl iodide (0.48 ml, 6 mM) and potassium carbonate (0.82 g, 6 mM) was stirred at room temperature for 12 hours. The mixture was concentrated to dryness and the residue was extracted with chloroform and water. The organic layer was washed with water, dried (MgSO4) and concentrated to dryness to give a solid. Recrystallization from 80% ethanol gave colorless needles (0.88 g, 50%), m.p. 146°-148° C.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. extractionthe residue was extracted with chloroform and water
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to dryness
  6. customto give a solid
  7. customRecrystallization from 80% ethanol

Sources & evidence

ORD record
ord-f64e473ba3c44aefa62e2d7b5d870c93
Source dataset
uspto-grants-1989_04
Patent number
US04824848

Reaction notes

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