Application of 1337532-51-0 ,Some common heterocyclic compound, 1337532-51-0, molecular formula is C7H7BrN4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
A mixture of 5-bromo-7-methyl-7/-/-pyrrolo[2,3-c]pyrimidin-4-amine (0.31 g, 1.37 mmol), 1- [4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]-2- pyrrolidinone (0.59 g, 1.37 mmol), Pd2(dba)3 (63 mg, 0.07 mmol) and K3P04 (0.63 g, 2.74 mmol) in 10 mL of dioxane and 3.3 mL of water in a 20 mL microwave vial was bubbled with argon for 10 min, and then tri-(t-butyl)phosphonium tetrafluoroborate (40 mg, 0.14 mmol) was added. The mixture was capped and heated in a metal matrix block at 100 C. After 18 h, LCMS showed conversion complete. The mixture was filtered. The filtrate was concentrated in vacuo. The residue was taken up in water (30 mL) to give a suspension, which was filtered. The solid cake was washed with water and ether. The cake was dried under house vacuum, dissolved in 10% MeOH in DCM. The organic was dried over Na2S04, filtered, and concentrated in vacuo. The residue was dissolved in 10% MeOH in DCM and was absorbed onto a dryload silica gel cartridge. Purification was performed on a 115 g silica gel cartridge using gradient elution of 1 % A to 60% A in CHCI3 (A was a mixture of 3200/800/80 CHCI3/MeOH/NH4OH). The desired product eluted from 25-30% A. The combined fractions containing pure product were concentrated in vacuo. The residue was dissolved in 10% MeOH in CHCI3 and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in 10% MeOH in DCM (12 mL), to which was added MTBE (15 mL). Solids slowly formed, resulting in a suspension. This mixture was concentrated in vacuo to reduce to half volume, followed by addition of another 15 mL of MTBE. The suspension was filtered. The cake was washed with MTBE (2 x 5 mL) and hexane (2 x 4 mL), dried under vacuum at 65 C for 20 h to afford 1-4-(4-amino-7-methyl- 7/-/-pyrrolo[2,3-c]pyrimidin-5-yl)phenyl)-3-(2,5-difluorophenyl)pyrrolidin-2-one (449 mg) as an off-white solid. LCMS (ES) m/z = 452 [M+H]+. H NMR (400 MHz, DMSOd6) delta ppm 2.22 – 2.35 (m, 1 H), 2.58 – 2.71 (m, 1 H), 3.75 (s, 3 H), 4.00 (dd, J=8.8, 5.3 Hz, 2 H), 4.17 (t, J=9.6 Hz, 1 H), 5.97 – 6.18 (br s, 1.2 H), 7.32 (s, 1 H), 7.49 (d, J=8.6 Hz, 2 H), 7.60 – 7.70 (m, 3 H), 7.73 (s, 1 H), 7.83 (d, J=8.8 Hz, 2 H), 8.16 (s, 1 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1337532-51-0, its application will become more common.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
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