Dimethylformamide → HCID 178437893, compound

HRID 1600823Notes

Reaction equation

HRID 1600823 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-1e5c2d49dc8844039618a498336f4661
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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