With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.163622-50-2, name is 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H5IN4, molecular weight is 260.04, as common compound, the synthetic route is as follows.category: pyrimidines
General procedure: Compound 6 (3.85 mmol), Pd(PPh3)4 (0.077 mmol), CuI (0.77 mmol), AmberliteIR-67, ethynylbenzene or 4-ethylphenylacetylene (4.6 mmol) in 30 mL of THF was heated for 30 min at 120 C in the microwave. After cooling to ambient temperature, the reaction mixture was filtered through a pad of Celite. The solvent was removed in vacuo, and the crude product was purified by flash column chromatography on silica gel (DCM/MeOH= 30/1) to give compound 7i or 7ii as a yellow solid.19 To a solution of 7i or 7ii (7.16 mmol) in DMF (20 mL) was added potassium carbonate (8.6 mmol) followed by 4-bromo-1-butene (8.6 mmol). After stirring at 30 C for 6 h, EtOAc (300 mL) was then added and the solution was washed three times with water. The combined organic phase was dried over Na2SO4 and concentrated. The residue was subjected to column chromatography on silica gel (DCM/MeOH= 30:1) to give compound 8i (83%) or 8ii (~56% yield over two steps). For 8i: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.51 – 7.49 (m, 2H), 7.43 – 7.33 (m, 3H), 7.22 (s, 1H), 5.90 (s, 2H), 5.79 – 5.72 (m, 1H), 5.08 (t, J = 16.2, 10.8 Hz, 2H), 4.26 (t, J = 7.2 Hz, 2H), 2.60 (q, J = 6.9 Hz, 2H); For 8ii: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.43 (d, J = 7.8 Hz, 2H), 7.20 – 7.18 (m, 3H), 5.92 (s, 2H), 5.82 – 5.73 (m, 1H), 5.17 (t, J =17.1, 9.9 Hz, 2H), 4.24 (t, J = 6.9 Hz, 2H), 2.75 – 2.52 (m, 4H), 1.24 (t, J = 7.5 Hz, 3H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,163622-50-2, 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine, and friends who are interested can also refer to it.
Reference:
Article; Wang, Chengyan; Liu, Hongchun; Song, Zilan; Ji, Yinchun; Xing, Li; Peng, Xia; Wang, Xisheng; Ai, Jing; Geng, Meiyu; Zhang, Ao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 11; (2017); p. 2544 – 2548;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia