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Stage #1: 4-pyridinecarboxylic acid, methyl ester; acetone With sodium methylate In diethyl ether for 6h; Heating / reflux;
Stage #2: With water; acetic acid
OO-1.1
Stepi: 1-Pyridin-4-ylbutane-1, 3-dione (oo-1); To a 500 mL flask with NaOMe (4.75 g) and anhydrous ether (130 mL) was sequentially added methyl isonicotinate (10.0 mL, 84.7 mmol), and a solution of acetone (12.4 mmol, 169 mmol) in ether {45 mL). The suspension was stirred at reflux for 6 hours, cooled, and filtered. The isolated solid was washed with ether and dissolved in water (40 mL). Glacial acetic acid (5.2 mL) was added and the mixture was extracted with chloroform (40 mL x 2). The organic extracts were dried over anhydrous Na2SO4 and concentrated to give the title compound oo-1 (8.6 g, 62% yield) as a brown solid, which was used without further purification. LCMS: 164.10 [M + H+]
60%
With sodium methylate In tetrahydrofuran 1.) RT, 30 min, 2.) reflux, 2.5 h;
Stage #1: 6-hydrazineylpyridine-3-sulfonamide; 1-(4-pyridyl)-1,3-butanedione With acetic acid at 110℃; for 1h;
Stage #2: With water; sodium hydrogencarbonate
OO-1.2
Step 2: 6-{3-Methyl-5-pyridin-4-yl-1 H-pyrazol-1-yl)pyridine-3-sulfonamide (OO-1 ); To 1-pyridin-4-ylbutane-1,3-dione 21-1 (245 mg, 1.50 mmol) in 1.5 mL of acetic acid was added6-hydrazinopyridine-3-sulfonamide {282 mg, 1.5 mmol). The mixture was heated at 11O0C for one hour and cooled, then basified to pH 7 with Sat. NaHCO3. The resultant solid was filtered, washed with water and hexane/ether (1 :1), then dried under vacuum to give the title compound U-1 (349 mg, yield 74%) as a light brown solid. Regiochemistry assumed from similar spectral data to compounds for literature, see
5-methyl-2-[4-(phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In hexane; dichloromethane; acetic acid
58 5-Methyl-2-[4-(phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile
EXAMPLE 58 5-Methyl-2-[4-(phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile A mixture of 4.8 g (0.03 moles) of 1-(4-pyridyl)-1,3-butanedione [J. Chem. Soc. (1950) p 1680], 8.4 g (0.03 moles) of 3-amino-5-(4-phenylmethyl-1-piperazinyl)-4-pyrazolecarbonitrile (prepared as described in Example 1) and 100 ml of glacial acetic acid was stirred at reflux for 18 hours. The resulting solution was evaporated in vacuo and gave an oil. The residue was partitioned between 100 ml of saturated sodium bicarbonate and 200 ml of dichloromethane. The organic layer was separated, dried over magnesium sulfate and passed through a short column of magnesium silicate. The elude was heated to boiling on a steam bath and 200 ml of hexane was added. The solution was concentrated by heating until a precipitate began to form. The mixture was then cooled at -10° C. and filtered. The precipitate was washed with hexane. The filtrate and wash was combined, concentrated to turbidity, cooled at -10° C. and filtered to collect the solid which was dried and gave 3.9 g of the desired product as a yellow solid, mp 179°-180° C.
5.A A.
A. 2-Bromo-2-(4-pyridyl)-1,3-butadione To a solution of 16.3 g (0.1 mole) of 1-(4-pyridyl)-1,3-butadione in 100 ml, 48% hydrobromic acid is slowly added 15.98 g (0.1 mol) bromine. The solution is stirred until the bromine color is discharged. The solution is evaporated to dryness to give the title compound.
With pyridine In methanol; water aq. soln. of Be sulfate added slowly to soln. of diketone and small amt.of pyridine in MeOH; ppt. filtered off and washed with water, recrystd, from 2-PrOH/CHCl3;
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