Water → HCID 178437893, compound

HRID 1600824Notes

Reaction equation

HRID 1600824 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.[H-].[Na+].[CH3:21]I.O>CN(C=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([S:16][CH3:21])=[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 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178437895HCID 178437895, compound

Product 1

HCID 178437893HCID 178437893, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alternatively, the product can be prepared as follows: To a stirred mixture of 1-cyclopentyl-3-ethyl-6-(thioxo) pyrazolo[3,4-d]pyrimidin-4-one (23.4 g, 0.09 mol) in DMF (250 mL) was added NaH (4.0 g, 0.1 mol., 60% dispersion in mineral oil) over 15 minutes. The resulting mixture was cooled in an ice bath, then methyl iodide (6.3 mL, 0.1 mol) was added over 20 minutes and the resulting mixture was stirred for 3 hours. The reaction mixture was poured into water (400 mL) and the precipitate which formed was collected by filtration, washed with water, then hexane and then was dried at 80-85° C. in a vacuum oven to afford 18.6 g (74%) of 1-cyclopentyl-3-ethyl-6-(methylthio)pyrazolo[3,4-d]pyrimidin-4-one, m.p.203-205° C.

Workup

  1. customAlternatively, the product can be prepared
  2. temperatureThe resulting mixture was cooled in an ice bath
  3. customthe precipitate which formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. dry with materialhexane and then was dried at 80-85° C. in a vacuum oven

Sources & evidence

ORD record
ord-3a2a199584d044fa89a9a3d1ea02b6c6
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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