Application of 151266-23-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 151266-23-8 as follows.
Example 13. l-(4-(4-amino-l-cyclopentyl-lH-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3- (3-(trifluoromethyl)phenyl)urea (AD60); [0182] A synthetic strategy for Cmpd AD60 is depicted in Scheme 8 following. Scheme 8[0183] Reagent 3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine) (0.5g; 1.9 mmol; Apsel et al., 2008, Id.) was combined with cyclopentyl iodide (0.24 mL; 2.1 mmol), l .Og K2CO3, in 20 mL DMF and heated to 45 C under argon for 2 hours. The reaction was filtered to remove solid K2CO3, and the filtrate was combined with brine and the organic product was extracted in CH2Cl2 (3x 50 mL). The combined organic layer was concentrated in vacuo and purified by silica gel chromatography (MeOH/Chloroform; 5:95) to afford l-cyclopentyl-3- iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 330.0, calculated 330.0). 4-nitrophenyl boronic acid (190 mg, 1.1 mmol; Sigma-Aldrich), was coupled to 1- cyclopentyl-3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (150mg, 0.456 mmol) via the Suzuki reaction in 6 mL 1,2 methoxy ethane, 1 mL of saturated sodium carbonate, 1.65 mL EtOH, and 200 mg of polymer-bound tetrakis palladium. The reaction was stirred under argon for 12 hours at room temperature, filtered through Whatman paper to remove palladium, mixed with brine, extracted in chloroform and the product was subsequently purified on silica in EtOAc and concentrated in vacuo. The purified solid l~cyclopentyl-3-(4- nitrophenyl)-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 325.0, calculated 325.1 ; lOOmg, 0.31 mmol) was combined with Zinc dust (605 mg, 9.25 mmol), 10 mL THF, 0.35 mL HOAc for 12 hours at room temperature under Argon. The reaction was filtered through CeIi te, extracted with EtOAc and concentrated in vacuo to yield 3-(4- aminophenyl)-l -cyclopentyl- lH-pyrazolo [3, 4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 295.0, calculated 295.2). To this reduced product, molar equivalents of3-(trifluoromethyl)phenyl isocyanate (Sigma-Aldrich) were added dropwise in ice-cold CH2C12. The reaction proceeded until completion as judged by TLC, was concentrated in vacuo, resuspended in 50:50 H20-CH3CN, and purified on a Cl 8 column in CH3CN/H20/0.1%TFA (1-100% gradient) to yield AD60 l-(4-(4-amino-l -cyclopentyl- IH- pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (ESI-MS m/z [M+H]+ found 482.2, calculated 482.0).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,151266-23-8, its application will become more common.
Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DAR, Arvin; SHOKAT, Kevan M.; WO2010/45542; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia