Dimethylformamide → HCID 178437893, compound

HRID 2257052Notes

Reaction equation

HRID 2257052 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12](=[S:16])[NH:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:17][CH3:18])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19]N(C=O)C.C([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>O>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([S:16][CH3:19])=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:17][CH3:18])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178437895HCID 178437895, compound

Product 1

HCID 178437893HCID 178437893, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-(thioxo)pyrazolo[3,4-d]pyrimidin-4-one (5.2 g, 19.6 mmol), DMF (50 mL) and K2CO3 (2.76 g, 20 mmol) was stirred at ambient temperature for 25 minutes and then dimethyl sulfate (3.88 mL, 40 mmol) was added. The reaction mixture was stirred for 2 hours, then was poured into cold water. The product was collected by filtration, washed with water, recrystallized from cyclohexane/ether and dried at 70°-75° C. in vacuo to afford 4.6 g of 1-cyclopentyl-3-ethyl-6-(methylthio)pyrazolo[3,4-d]pyrimidin-4-one, m.p.200°-202° C.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customrecrystallized from cyclohexane/ether
  5. customdried at 70°-75° C. in vacuo

Sources & evidence

ORD record
ord-57ac98b619a9414798c689510d00e6a3
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

Loading…