p-Toluenesulfonic acid → 7,8-Dihydro-1,3,5,7,7-pentamethyl-1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidine

HRID 2417665Notes

Reaction equation

HRID 2417665 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=C[CH:2]=1.[NH2:12][CH2:13][C:14]([NH2:17])([CH3:16])[CH3:15].[NH2:18][C:19]1[C:20]([CH3:27])=[N:21][N:22]([CH3:26])[C:23]=1[C:24]#N.[OH-].[NH4+]>C(Cl)(Cl)Cl>[CH3:26][N:22]1[C:23]2[C:24]3[N:17]([C:14]([CH3:16])([CH3:15])[CH2:13][N:12]=3)[C:1]([CH3:2])=[N:18][C:19]=2[C:20]([CH3:27])=[N:21]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 131282-MethylpropylenediamineHCID 14923Ammonium HydroxideHCID 123358164-Amino-1,3-dimethyl-1H-pyrazole-5-carbonitrile

Product 1

HCID 204475447,8-Dihydro-1,3,5,7,7-pentamethyl-1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The requisite 2-(4-amino-1,3-dimethyl-5-pyrazolyl)-3,3-dimethylimidazoline is prepared as follows. p-Toluenesulfonic acid (10 g, 0.055 mol) is added to 5 g (0.057 mol) of 1,2-diamino-2-methylpropane and to the resulting hot (100°) melt is added 7 g (0.05 mol) of 4-amino-5-cyano-1,3-dimethylpyrazole. The mixture is heated in an oil bath at 185°-195° C. for six hours. The residue, an amorphous yellow solid is dissolved in 250 ml of chloroform and stirred with 40 ml of conc. ammonium hydroxide. The organic layer is separated, dried (MgSO4), and evaporated in vacuo to give 9 g (90%) of slightly crude title compound as a viscous purple oil.

Workup

  1. temperatureThe mixture is heated in an oil bath at 185°-195° C. for six hours
  2. customThe organic layer is separated
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-dacc3ed4d1254f1dbcdcbb7c4a8d190c
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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