Sodium hydride → HCID 14838104, compound

HRID 1165784Notes

Reaction equation

HRID 1165784 reaction equation
[CH2:1]([N:5]1[C:10]2=[N:11][N:12]([CH2:16][CH2:17][CH2:18][CH2:19]Cl)[C:13]([NH:14][CH3:15])=[C:9]2[C:8](=[O:21])[N:7]([CH2:22][CH2:23][CH3:24])[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].[H-].[Na+]>CN(C=O)C>[CH2:1]([N:5]1[C:10]2=[N:11][N:12]3[CH2:16][CH2:17][CH2:18][CH2:19][N:14]([CH3:15])[C:13]3=[C:9]2[C:8](=[O:21])[N:7]([CH2:22][CH2:23][CH3:24])[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 14838071HCID 14838071, compound

Product 1

HCID 14838104HCID 14838104, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-butyl-2-(4-chlorobutyl)-3-methylamino-5-propyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione(2.0 g) in DMF(30 ml) was added sodium hydride(60% oil, 0.65 g) in portions under ice-cooling. The mixture was stirred at room temperature for further 5 hours. The reaction mixture was concentrated to dryness and was added to ice-water, followed by neutralizing with 1N-HCl and extraction with chloroform. The chloroform layer was washed with water, dried and concentrated to dryness to give a syrupy product. The product was purified by flash chromatography(silica gel, chloroform) to give crystals, which recrystallized from isopropyl ether/hexane to afford colorless crystals(1.2 g, 67%), m.p. 63°-65° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additionwas added to ice-water
  4. extractionby neutralizing with 1N-HCl and extraction with chloroform
  5. washThe chloroform layer was washed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. customto give a syrupy product
  9. customThe product was purified by flash chromatography(silica gel, chloroform)
  10. customto give crystals, which
  11. customrecrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-d7a788aa26c845038aec15de17215eb8
Source dataset
uspto-grants-1990_03
Patent number
US04912104

Reaction notes

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