N,N-Dimethylaniline → HCID 21416630, compound

HRID 442111Notes

Reaction equation

HRID 442111 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 were slowly added 48 grams of N,N-dimethylaniline. The mixture was heated under reflux for two 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 two 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-9e518b375d604e10acf24b995deb1d52
Source dataset
uspto-grants-1977_08
Patent number
US04044130

Reaction notes

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