4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)benzoic acid synthesis
- Product Name:4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)benzoic acid
- CAS Number:1401728-86-6
- Molecular formula:C18H19N3O2
- Molecular Weight:309.36
![4-[(5-amino-3-ethyl-1H-pyrazol-4-yl)methyl]benzonitrile](/CAS/20180703/GIF/1401728-85-5.gif)
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Yield:-
Reaction Conditions:
with hydrogenchloride;water;acetic acid at 110; for 43 h;
Steps:
29.5.E Step E: 4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)benzoic acid (27)
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. 1H NMR (500 MHz, DMSO-d6) δ (ppm): 12.61-12.89 (s, br, 1H), 7.83 (d, 2H), 7.30 (d, 2H), 6.81 (s, 1H), 4.11 (d, 2H), 2.67 (m, 2H), 2.63 (s, 3H), 2.48 (s, 3H), 1.12 (t, 3H).
References:
US2012/252778,2012,A1 Location in patent:Paragraph 0325-0326
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