ChemicalBook CAS DataBase List (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine

(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine synthesis

7synthesis methods

Product Name:(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine
CAS Number:1223404-90-7
Molecular formula:C16H13F2N5O2
Molecular Weight:345.3

(2R)-2-(2,5-difluorophenyl)-1-{pyrazolo[1,5-a]pyrimidin-5-yl}pyrrolidine

1223404-89-4
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(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine

1223404-90-7
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Yield:1223404-90-7 58%

Reaction Conditions:

with nitric acid;trifluoroacetic acid at 20;

Steps:

B.B
Step B: Preparation of (RV5-(2-(2.5-difluorophenvnpyrrolidin-l-yr)-3- nitropyrazolo [ 1 ,5 -alpyrimidine; (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-l-yl)pyrazolo[l,5- ajpyrimidine (3.3 g, 10.99 mmol), was dissolved in 25 mL TFA at ambient temperature to give a clear yellowish solution, then nitric acid (3.434 mL, 54.94 mmol) was added drop-wise to the solution with rapid stirring. After addition, the reaction mixture was stirred for another 15 minutes at ambient temperature, then quenched by pouring onto ice with rapid stirring. The resulting yellowish suspension was filtered, rinsed with water, then the solid was triturated with MeOH (50 mL, with brief sonication), and vacuum-filtered, giving the pure product as a fine off-white powder (2.2 g, 58% yield).

References:

ARRAY BIOPHARMA INC.;HAAS, Julia;ANDREWS, Steven, W.;JIANG, Yutong;ZHANG, Gan WO2010/48314, 2010, A1 Location in patent:Page/Page column 46

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