Acetic Acid → 3-Isopropylpyrazolo[1,5-a]pyrimidin-2-amine

HRID 1912915Notes

Reaction equation

HRID 1912915 reaction equation
C(O)(=O)C.CN(C)[CH:7]=[CH:8][CH:9]=O.[CH:12]([C:15]1[C:16]([NH2:21])=[N:17][NH:18][C:19]=1[NH2:20])([CH3:14])[CH3:13]>C(O)C>[CH:12]([C:15]1[C:16]([NH2:21])=[N:17][N:18]2[CH:9]=[CH:8][CH:7]=[N:20][C:19]=12)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 791253-(Dimethylamino)-2-propenalHCID 687569004-Isopropyl-1H-pyrazole-3,5-diamine

Product 1

HCID 687533643-Isopropylpyrazolo[1,5-a]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetic acid (0.038 mL, 0.67 mmol) was added to a solution of 3-dimethylaminoacrylaldehyde (624 mg, 4.43 mmol) and the product from Example 112B (414 mg, 2.95 mmol) in ethanol (9 mL), and the reaction mixture was heated at 80° C. for 4 hours, then concentrated under vacuum to a dark oil. The residue was purified by flash chromatography (silica gel eluted with hexanes-EtOAc 50:50-0:100) to provide the title compound as a yellow solid. MS (ESI) m/z 177 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum to a dark oil
  2. customThe residue was purified by flash chromatography (silica gel eluted with hexanes-EtOAc 50:50-0:100)

Sources & evidence

ORD record
ord-cb5fb8cc43584eff817502576e90964f
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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