N,N-Diethylaniline → 7-Chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[N:5]([N:9]=[CH:10][C:11]=2[C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[C:6](=O)[CH:7]=1.CCN(C1C=CC=CC=1)CC.O=P(Cl)(Cl)[Cl:34]>>[Cl:34][C:6]1[N:5]2[N:9]=[CH:10][C:11]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=1Participants
4
Procedure
A suspension of 5-methyl-3-(2,4,6-trimethyl-phenyl)-4H-pyrazolo[1,5-a]pyrimidin-7-one (590 mg, 2.2 mmol) in 9 ml of POCl3 was treated with diethylaniline (0.7 ml) and the resulting mixture was stirred at reflux for 15 hours. The reaction mixture was concentrated to dryness. The residue was treated with ice water and stirred for 20 min, then extracted with chloroform. The organic layer was dried and concentrated to yield an orange oil which crystallized upon standing. The material was purified through silica gel column chromatography using chloroform as eluent to give 590 mg (94%) of the title compound as a yellow solid; 1H NMR (CDCl3) ä 8.08(s, 1H), 6.98(s, 2H), 6.86(s, 1H), 2.56(s, 3H), 2.33(s, 3H), 2.09(s, 6H) ppm.
Workup
- temperatureat reflux for 15 hours
- concentrationThe reaction mixture was concentrated to dryness
- additionThe residue was treated with ice water
- stirringstirred for 20 min
- extractionextracted with chloroform
- customThe organic layer was dried
- concentrationconcentrated
- customto yield an orange oil which
- customcrystallized
- customThe material was purified through silica gel column chromatography
Sources & evidence
- ORD record
- ord-b4c97d249f0e47ec8426266db4209f38
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900217B2
Reaction notes
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