Dimethylformamide → HCID 178437893, compound

HRID 1736593Notes

Reaction equation

HRID 1736593 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+].COS(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, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-thioxopyrazolo[3,4-d]pyrimidin-4-one (5.2 g, 19.6 mmol), DMF (50 ml) and K2CO3 (2.8 g, 20 mmol) was stirred at ambient temperature for 25 minutes. The mixture was then treated with dimethylsulfate (3.8 ml, 40 mmol) and was stirred for 2 hours. The reaction mixture was poured into water and the resulting white precipitate was collected by filtration and washed with water. The product was recrystallized from cyclohexane/ether and dried in high vacuum at 70°-75° C. to afford 4.6 g (85%) of 1-cyclopentyl-3-ethyl-6-methylthiopyrazolo[3,4-d]pyrimidin-4-one as cream colored needles, m.p. 200°-202° C.

Workup

  1. stirringwas stirred for 2 hours
  2. filtrationthe resulting white precipitate was collected by filtration
  3. washwashed with water
  4. customThe product was recrystallized from cyclohexane/ether
  5. customdried in high vacuum at 70°-75° C.

Sources & evidence

ORD record
ord-124117a004fe46ebafa7139c81c06e4d
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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