Benzylamine → 5-Chloro-3-(1-methylethyl)-N-(phenylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 1892158Notes

Reaction equation

HRID 1892158 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][C:11]([CH:12]([CH3:14])[CH3:13])=[C:4]2[N:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCO>[CH2:15]([NH:22][C:6]1[N:5]2[N:9]=[CH:10][C:11]([CH:12]([CH3:14])[CH3:13])=[C:4]2[N:3]=[C:2]([Cl:1])[CH:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 210656445,7-Dichloro-3-(propan-2-yl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 251233625-Chloro-3-(1-methylethyl)-N-(phenylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,7-dichloro-3-isopropylpyrazolo[1,5-α]pyrimidine (500 mg, 2.17 mmol) and benzyl amine (0.52 mL, 4.78 mmol) in EtOH (20 mL) were refluxed for about 3 hours. The reaction mixture was then cooled to ambient temperature and concentrated in vacuo. The remaining residue was purified by flash chromatography on silica (methanol/ethyl acetate) to yield N-benzyl-5-chloro-3-isopropylpyrazolo[1,5-α]pyrimidin-7-amine as a white solid in analytically pure form (630 mg, 97%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe remaining residue was purified by flash chromatography on silica (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-bfc59b9a9a51418ab06fa471f5f32279
Source dataset
uspto-grants-2013_08
Patent number
US08507673B2

Reaction notes

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