1,2-Hydrazinedicarboxaldehyde → HCID 135815276, compound

HRID 1977626Notes

Reaction equation

HRID 1977626 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[NH:8][C:9](=[O:20])[C:10]3[N:15]([CH3:16])[N:14]=[C:13]([CH2:17][CH2:18][CH3:19])[C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH:23](NNC=O)=[O:24]>ClCCl>[CH3:16][N:15]1[C:10]2[C:9](=[O:20])[NH:8][C:7]([CH2:6][C:5]3[CH:21]=[CH:22][C:2]([NH:1][CH:23]=[O:24])=[CH:3][CH:4]=3)=[N:12][C:11]=2[C:13]([CH2:17][CH2:18][CH3:19])=[N:14]1

Participants

4

Reactant 2

HCID 123421,2-HydrazinedicarboxaldehydeHCID 1358152625-[(4-Aminophenyl)methyl]-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 135815276HCID 135815276, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 5-(4-aminobenzyl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]-pyrimidin-7-one (297 mg, 0.0010 mol) and 1,2-diformylhydrazine (101 mg, 0.00115 mol) was heated to 200° C. The resulting melt was then stirred under a nitrogen atmosphere at this temperature for 55 minutes. On cooling, the solid was dissolved in dichloromethane:methanol, pre-absorbed onto silica and purified by flash column chromatography eluting with a solvent gradient of dichloromethane:methanol (99:1 to 96:4 by volume) then dichloromethane:methanol:0.880 aqueous ammonia (90:10:1 by volume). Crystallisation from ethyl acetate/methanol gave the title compound (170 mg), m.p.260-261° C.

Workup

  1. temperatureOn cooling
  2. custommethanol, pre-absorbed onto silica
  3. custompurified by flash column chromatography
  4. washeluting with a solvent gradient of dichloromethane:methanol (99:1 to 96:4 by volume)
  5. customCrystallisation from ethyl acetate/methanol

Sources & evidence

ORD record
ord-3547ab20b1c54760b3f9540d2a7b684a
Source dataset
uspto-grants-2001_05
Patent number
US06235742B1

Reaction notes

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