Acetic Acid → 3-(2,3-Dichlorobenzyl)-2-methyl-5-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-ol acetate

Reaktionsgleichung

[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[C:6]([CH3:11])=[N:7][NH:8][C:9]=1[NH2:10].O=[C:18]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=O.C(O)(=[O:33])C>>[C:23]([O:22][C:20]1[N:8]2[N:7]=[C:6]([CH3:11])[C:5]([CH2:4][C:3]3[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:2]=3[Cl:1])=[C:9]2[N:10]=[C:18]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:19]=1)(=[O:33])[CH3:24]

Komponenten

Edukt 3

HCID 176Acetic Acid

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

HCID 178434675HCID 178434675, Verbindung

Produkt 1

HCID 712709503-(2,3-Dichlorobenzyl)-2-methyl-5-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-ol acetateAusbeute 60 %

Versuchsvorschrift

A mixture of 4-(2,3-dichlorobenzyl)-3-methyl-1H-pyrazol-5-amine (1.21 g, 4.72 mmol), ethyl 3-oxo-3-(pyridin-4-yl)propanoate (1.004 g, 5.195 mmol) in acetic acid (50 mL) was stirred under reflux overnight. After cooled to room temperature, the mixture was concentrated. The residue was diluted with ethyl acetate (20 mL). The resulting precipitate was filtered, washed with ethyl acetate, dried in vacuo to give the titled product (1.266 g, 60%); LC/MS: MS (ES+) m/e 385 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 1.91 (s, 3H), 2.12 (s, 3H), 4.16 (s, 2H), 6.10 (s, 1H), 6.91 (dd, J=1.2, 7.8 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.51 (dd, J=1.2, 7.8 Hz, 1H), 7.77 (d, J=5.7 Hz, 2H), 8.77 (d, J=5.7 Hz, 2H), 11.94 (s, 1H), 12.18 (s, 1H).