81765-97-1 | Pyrimidines

Brief introduction of 4-Chloro-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 81765-97-1, 4-Chloro-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Related Products of 81765-97-1 ,Some common heterocyclic compound, 81765-97-1, molecular formula is C11H11ClN2S, 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.

To the solution of 4-amino-2-fluorophenol (41 mg, 0.32 mmol) in dried DMF (3 mL), was added NaH (13 mg, 0.54 mmol). The mixture was stirred at 0 °C for 10 min, and then a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine 4i (50 mg, 0.19 mmol) in dried DMF (1 mL) was added. The mixture was stirred at 0 °C for 1.5 h. Ice water (5 mL) was added to quench the reaction and the mixture was extracted by Et2O (3 .x. 10 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatograph.

Reference:
Article; Zhao, Ailing; Gao, Xin; Wang, Yuanxiang; Ai, Jing; Wang, Ying; Chen, Yi; Geng, Meiyu; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 19; 13; (2011); p. 3906 – 3918;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A new synthetic route of 81765-97-1

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 81765-97-1, 4-Chloro-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine.

Application of 81765-97-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 81765-97-1, name is 4-Chloro-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine, molecular formula is C11H11ClN2S, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of compound 4 (0.65 mmol) or compound 27, compound 5 (0.73 mmol) and sodium bicarbonate (1.30 mmol) in DMSO (5 mL) was stirred at 80 C for 16 h. The mixture was extracted with ethyl acetate. The extract was washed with saline and the solvents were removed in vacuo. The crude product was purified by silica gel chromatography using cyclohexane-ethyl acetate(25:1) as eluate to give compound 6-13 or compound 28 (63% yield) as white solid. 2-Methyl-4-((1-phenyl-1H-tetrazol-5-yl)thio)-5,6,7,8-tetrahydrobenzo [4,5]thieno[2,3-d]pyrimidine (6). Yield=36%; 1H NMR (500 MHz, CDCl3) delta 7.63 (dt, J=8.4, 3.6 Hz, 2H), 7.55-7.44 (m, 3H), 3.04 (t, J=4.8 Hz, 2H), 2.86 (d, J=5.2 Hz, 2H), 2.45 (s, 3H), 1.99-1.88 (m, 4H), 1.28 (s, 1H). 13C NMR (126 MHz, CDCl3) delta 167.74 (s), 161.14 (s), 155.98 (s), 146.50 (s), 137.61 (s), 134.23 (s), 130.44 (s), 129.40 (s), 125.90 (d, J=14.9 Hz), 124.53 (s), 29.70 (s), 26.07 (s), 25.72 (s), 25.21 (s), 22.42 (d, J=12.8 Hz). ESI-MS m/z: 381.2 [M+H]+.

Reference:
Article; Lao, Chuyu; Zhou, Xiaoqing; Chen, Huanpeng; Wei, Fengjiao; Huang, Zhaofeng; Bai, Chuan; Bioorganic Chemistry; vol. 90; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The origin of a common compound about 81765-97-1

General procedure: The different 4-chloro-thieno[2,3-d]pyrimidine (7a-d or f-i) (1 eq.) was suspended in MeOH (5.1mL/mmol eq.) and hydrazine hydrate 80percent in water (2 eq.) and the mixture was refluxed for 5 h. Immediately after, hydrazine hydrate (2 eq.) was added to complete the reaction and the mixture was allowed to reflux for further 3 h. The reaction mixture was then cooled to r.t and placed in a fridge o.n. The resulting precipitate was filtered and crystallised from a solution of 40percent EtOH in water unless otherwise stated.

Reference:
Article; Bassetto, Marcella; Leyssen, Pieter; Neyts, Johan; Yerukhimovich, Mark M.; Frick, David N.; Brancale, Andrea; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 31 – 47;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia