Benzhydrylidene-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-amine → 4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenylamine

HRID 403490Notes

Reaction equation

HRID 403490 reaction equation
C(=[N:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[C:23]([CH2:33][CH3:34])=[N:24][N:25]3[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[N:27][C:26]=23)=[CH:17][CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1>O.CCO.Cl>[CH2:33]([C:23]1[C:22]([CH2:21][C:18]2[CH:17]=[CH:16][C:15]([NH2:14])=[CH:20][CH:19]=2)=[C:26]2[N:27]=[C:28]([CH3:32])[CH:29]=[C:30]([CH3:31])[N:25]2[N:24]=1)[CH3:34]

Participants

5

Reactant 1

HCID 86671753Benzhydrylidene-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-amine

Product 1

HCID 683791594-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenylamine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Benzhydrylidene-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-amine (12) (3.97 g, 8.93 mmol) was dissolved in a mixture of water (40 ml), EtOH (10 ml) and conc. HCl (10 ml) and stirred at rt for 1 h. The reaction mixture was basified to pH 11 with Na2 CO3. The organic layer was extracted with EtOAc, washed with water and brine, dried over Na2 SO4 and concentrated to afford an orange oil. The crude product was purified by chromatography (2-50% EtOAc in cyclohexane) to afford a yellow solid.

Workup

  1. extractionThe organic layer was extracted with EtOAc
  2. washwashed with water and brine
  3. customdried over Na2 SO4
  4. concentrationconcentrated
  5. customto afford an orange oil
  6. customThe crude product was purified by chromatography (2-50% EtOAc in cyclohexane)
  7. customto afford a yellow solid

Sources & evidence

ORD record
ord-d6ff6f2163364cec8b9e6602626960e0
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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