1H-Pyrazol-3-amine, 5-methyl- → 1-(2,7-Dimethylpyrazolo[1,5-a]pyrimidin-6-yl)ethan-1-one

HRID 1271384Notes

Reaction equation

HRID 1271384 reaction equation
C[N:2]([CH:4]=[C:5]([C:9](=O)[CH3:10])[C:6](=[O:8])[CH3:7])[CH3:3].NC1[CH:17]=[C:16]([CH3:18])[NH:15][N:14]=1>C(O)C>[CH3:18][C:16]1[CH:17]=[C:3]2[N:2]=[CH:4][C:5]([C:6](=[O:8])[CH3:7])=[C:9]([CH3:10])[N:14]2[N:15]=1

Participants

4

Reactant 2

HCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 5670033-[(Dimethylamino)methylidene]pentane-2,4-dione

Product 1

HCID 6392521-(2,7-Dimethylpyrazolo[1,5-a]pyrimidin-6-yl)ethan-1-oneYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-dimethylaminomethylene-pentane-2,4-dione (4 g, 25.8 mmol) and 3-amino-5-methylpyrazole (2.45 g, 24.5 mmol) in ethanol (50 mL) was heated to reflux for 2 hrs, then cooled to ambient temperature and stirred over night. The solid precipitate was collected by filtration and washed with cold ethanol (50 mL). The solid was dried under vacuum to provided 3.8 g of the title compound. 1H NMR (300 MHz, CD3OD) δ 2.52 (s, 3 H), 2.68 (s, 3 H), 3.07 (s, 3 H), 6.55 (s, 1 H), 6.87 (s, 1 H); MS (DCl/NH3) m/z 190 (M+H)+.

Workup

  1. temperatureto reflux for 2 hrs
  2. filtrationThe solid precipitate was collected by filtration
  3. washwashed with cold ethanol (50 mL)
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-230292eb6883497bb5abed5d9370ea91
Source dataset
uspto-grants-2007_04
Patent number
US07205316B2

Reaction notes

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