N,N-Dimethylaniline → HCID 21416630, compound

HRID 1604936Notes

Reaction equation

HRID 1604936 reaction equation
[CH3:1][N:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[C:4]([C:12]2[O:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[N:3]1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:31])=O>>[Cl:31][C:10]1[N:9]=[CH:8][N:7]=[C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:12]3[O:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=3)[C:5]=12

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 135850753HCID 135850753, compound

Product 1

HCID 21416630HCID 21416630, compound

Procedure

To a mixture of 5.0 grams of 1-methyl-3-(5-nitro-2-furyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)one and 100 milliliters of phosphorus oxychloride was slowly added 48 grams of N,N-dimethylaniline. The mixture was heated under reflux for 2 hours, cooled and carefully added to 1 kilogram of crushed ice. The crystalline product was collected, washed with ether and dried. Recrystallisation from ethyl acetate gave 4-chloro-1-methyl-3-(5-nitro-2-furyl)-1H-pyrazolo[3,4-d]pyrimidine having melting point 195°C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. customThe crystalline product was collected
  5. washwashed with ether
  6. customdried
  7. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-6b73b936962b49e89e6ddc4f624dc506
Source dataset
uspto-grants-1976_04
Patent number
US03948913

Reaction notes

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