Acetic Acid → 4-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)benzoic acid

HRID 403502Notes

Reaction equation

[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][CH3:8])[C:3]=1[CH2:9][C:10]1[CH:17]=[CH:16]C(C#N)=[CH:12][CH:11]=1.[CH3:18][C:19](=O)[CH2:20][C:21](=O)[CH3:22].[CH3:25][C:26]([OH:28])=[O:27].Cl>O>[CH2:7]([C:4]1[C:3]([CH2:9][C:10]2[CH:11]=[CH:12][C:25]([C:26]([OH:28])=[O:27])=[CH:16][CH:17]=2)=[C:2]2[N:1]=[C:19]([CH3:18])[CH:20]=[C:21]([CH3:22])[N:6]2[N:5]=1)[CH3:8]

Participants

Conditions

Temperature: 110 °C

Procedure

To a 500 ml, four-necked flask equipped with an overhead stirrer, a thermocouple and a condenser was charged with 4-((5-amino-3-ethyl-1H-pyrazol-4-yl)methyl)benzonitrile (26) (12.8 g, 56.5 mmol), pentane-2,4-dione (6.8 g, 67.9 mmol, 1.2 eq), 20 ml of HOAc and 40 ml of concentrated HCl. The mixture was stirred at 110° C. for 43 hours. It was cooled to room temperature and 300 ml of water was added. Slowly, the solution became a suspension. It was stirred at room temperature for 1 h. The precipitate was collected by vacuum filtration and the solid was washed with water. The solid was vacuum oven dried at 50° C. for 5 h.

Workup

customTo a 500 ml, four-necked flask equipped with an overhead stirrer
temperatureIt was cooled to room temperature
stirringIt was stirred at room temperature for 1 h
filtrationThe precipitate was collected by vacuum filtration
washthe solid was washed with water
customdried at 50° C. for 5 h.

Sources & evidence

ORD record: ord-ccdcca48327648ba9fc838eb0bae381b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748435B2

Reaction notes

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