Acetylacetone → 3-Isopropyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amine

HRID 1912924Notes

Reaction equation

HRID 1912924 reaction equation
[C:1]([CH2:4][C:5](=O)[CH3:6])(=O)[CH3:2].[CH:8]([C:11]1[C:12]([NH2:17])=[N:13][NH:14][C:15]=1[NH2:16])([CH3:10])[CH3:9].Cl.NO>C(O)(=O)C>[CH:8]([C:11]1[C:15]([NH2:16])=[N:14][N:13]2[C:1]([CH3:2])=[CH:4][C:5]([CH3:6])=[N:17][C:12]=12)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 31261AcetylacetoneHCID 443297Hydroxyamine hydrochlorideHCID 687569004-Isopropyl-1H-pyrazole-3,5-diamine

Product 1

HCID 687489893-Isopropyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of acetylacetone (1034 mg, 10.33 mmol) and the product from Example 112B (965 mg, 6.88 mmol) in acetic acid (5 mL) was heated at 115° C. for 90 minutes, and then cooled to room temperature. Hydroxylamine hydrochloride (520 mg) was added, and the solution was stirred at room temperature for 14 hours, and then concentrated under vacuum. The residue was purified by HPLC (30×100 mm XBridge column eluted with 0.1 M aqueous (NH4)2CO3-MeOH, 60:40-0:100 over 15 min) to provide the title compound. MS (DCI/NH3) m/z 205 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by HPLC (30×100 mm XBridge column eluted with 0.1 M aqueous (NH4)2CO3-MeOH, 60:40-0:100 over 15 min)

Sources & evidence

ORD record
ord-ebe9207079224b71ab60b3c661079019
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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