Category: 163622-50-2

Synthetic Route of 163622-50-2, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 163622-50-2, name is 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

4-amino-5-iodo-weighed -7H- pyrrolo [2,3-d] pyrimidine (2g, 0.0077mol)And potassium carbonate (4.2 g, 0.0310 mol),After adding DMF (50mL) dissolved and heated to 90 reflux,N-Butyl iodide (2 mL) was added dropwise to the solution using a separatory funnel.After 3 hours of reaction, the solvent was evaporated, extracted with ethyl acetate,The organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure.And purified by column chromatography to give 1.80 g of a white solid (74% yield).

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:
Patent; Sichuan University Huaxi Hospital; He Yang; Chai Yingying; Chen Bojiang; Zhou Xinglong; Li Changfu; Qiu Zhixin; Li Weimin; (11 pag.)CN106831790; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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

Reference of 163622-50-2 , The common heterocyclic compound, 163622-50-2, name is 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H5IN4, 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.

Dissolve 3-iodo-4-amino-1H-pyrrole [3,4-d] pyrimidine (294 mg, 1.13 mmol) in 2 mL (1: 3) of a mixed solvent of ethanol and DME, and then add 0.25 mL of saturated sodium carbonate Solution andN-methyl 2-azaindole-3-boronic acid pinacol ester (413 mg, 1.6 mmol). After the whole system was ventilated three times, tetrakis (triphenylphosphine) palladium (127 mg, 0.11 mmol) was added to the mixture, and then the whole system was heated to 90 C. under nitrogen and stirred for 12 hours. After the reaction was completed, filtration was performed with celite, and the obtained filtrate was washed three times with water and dichloromethane. The organic phase was subjected to rotary evaporation under reduced pressure to obtain a solid, which was separated by silica gel column chromatography (eluent was dichloromethane containing 1-2% methanol), and finally 234 mg (0.88 mmol) of the target compound was obtained as a pale green solid. Yield: 78%.

The synthetic route of 163622-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yaoya Science And Technology (Shanghai) Co., Ltd.; Liang Yonghong; Zeng Zhaosen; Ling Yuan; (35 pag.)CN110452243; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia