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

HRID 510419Notes

Reaction equation

HRID 510419 reaction equation
[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]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 178434675HCID 178434675, compound

Product 1

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

Procedure

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).

Workup

  1. temperatureunder reflux overnight
  2. concentrationthe mixture was concentrated
  3. additionThe residue was diluted with ethyl acetate (20 mL)
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-415fccffbb4a46c1a04bfabb638a0e1b
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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