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

HRID 510416Notes

Reaction equation

HRID 510416 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])=[C:5]([NH2:15])[NH:4][N:3]=1.O=[C:17]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=O.C(O)(=[O:32])C>>[C:22]([O:21][C:19]1[N:4]2[N:3]=[C:2]([CH3:1])[C:6]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH3:14])=[C:5]2[N:15]=[C:17]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:18]=1)(=[O:32])[CH3:23]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 178424217HCID 178424217, compound

Product 1

HCID 712708962-Methyl-3-(2-methylbenzyl)-5-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-ol acetateYield 69%

Procedure

A solution of 3-methyl-4-(2-methylbenzyl)-1H-pyrazol-5-amine (3.005 g, 14.93 mmol) and ethyl 3-oxo-3-(pyridin-4-yl)propanoate (3.17 g, 16.42 mmol) in acetic acid (50 mL) was stirred under reflux for 48 h. After cooled to room temperature, the mixture was concentrated. The residue was diluted with ethyl acetate (30 mL). The resulting precipitate was filtered, washed with ethyl acetate, dried in vacuo to give the titled product (4.02 g, 69%); LC/MS: MS (ES+) m/e 331 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 1.91 (s, 3H), 2.09 (s, 3H), 2.36 (s, 3H), 3.99 (s, 2H), 6.08 (s, 1H), 6.78 (d, J=7.8 Hz, 1H), 7.04-7.21 (m, 3H), 7.77 (d, J=4.8 Hz, 1H), 8.76 (d, J=4.8 Hz, 1H), 11.95 (s, 1H), 12.16 (s, 1H).

Workup

  1. temperatureunder reflux for 48 h
  2. concentrationthe mixture was concentrated
  3. additionThe residue was diluted with ethyl acetate (30 mL)
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4e58cdd20fc14417b810ebc43aba9932
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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