Category: 955368-90-8

Reference of 955368-90-8 , The common heterocyclic compound, 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, molecular formula is C9H10N4OS, 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.

Into a 25 mL microwave vial was added 2-allyl-6-(methylthio)-1H-pyrazolo[3,4- d]pyrimidin-3(2H)-one (275 mg, 1.235 mmol) (obtained according to EP2213673B1, Production Example 1, p37), [(5-bromopyridin-3-yl)imino]dimethyl-A6-sulfanon (400 mg, 1.61 mmol), potassium carbonate (239 mg, 1.73 mmol) and dioxane (5 mL). The resultant suspension was degassed (bubbling of N2) and copper (I) iodide (235 mg, 1.235 mmol) was added followed by N1,N2-dimethylethane-1,2-diamine (0.133 mL,1.24 mmol). The vial was capped and the reaction mixture was stirred at 95 00 overnight. After cooling to RT the reaction mixture was transferred to a separation funnel, NH4OH (aq, 20 mL) was added and the resulting mixture was extracted with EtOAc (3 x 30 mL). The organic phases were combined, dried and evaporated under vacuum. The residue was purified using flash chromatography (0-15% MeOH in EtOAc). The product containing fractions were concentrated to give the title compound (60 mg, 12.44 % yield) as an yellowish oil that solidified upon storage. LCMS (Method C): RT = 0.99 mi mlz = 391 [M+H].1H NMR (300 MHz, ODd3) O 9.21 (5, 1H), 8.64 (5, 1H), 8.57 (5, 1H), 8.12 (5, 1H),5.70-5.41 (m, 1H), 5.17 (t, J = 5.1 Hz, 1H), 4.96 (d, J = 17.0 Hz, 2H), 4.53 (d, J = 6.0 Hz, 2H), 3.31 (5, 6H), 2.53 (5, 3H)

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BURKAMP, Frank; ROUNTREE, James Samuel Shane; TREDER, Adam Piotr; (155 pag.)WO2018/11569; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 955368-90-8, 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. 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one. A new synthetic method of this compound is introduced below.

Cuprous iodide (42.82 mg, 224.85 mumol), N,N’-dimethyllethylenediamine (22.20 mg, 251.83 mumol, 27.07 muL) and potassium carbonate (42.88 mg, 310.29 mumol) were added separately into the compound I1 (49.98 mg, 224.85 mumol) and 72-1 (56.00 mg, 224.85 mumol) in dioxane (3 mL) solution, the reaction mixture was stirred at 95C for 1 hour under nitrogen atmosphere, then concentrated and added 20 mL ammonia, extracted by EA 150 mL (50 mLx3) and washed by saturated brine 30 mL, dried over anhydrous sodium sulfate, then filtered to give the crude compound. The crude product was purified by silica gel column chromatography (PE/EA=3/1) 72-1. MS m/z: 391.0 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,955368-90-8, 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

Compound 1.1 (255 mg, 1 mmol),2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (222 mg, 1 mmol),Cuprous iodide (191 mg, 1 mmol),Anhydrous potassium carbonate (276 mg, 2 mmol)And N,N-dimethylethylenediamine (88 mg, 1 mmol)Add to 1,4-dioxane (20 mL),The reaction system was stirred at 100 C overnight.The reaction solution was then cooled to room temperature.filter,The filtrate is concentrated,The residue was purified by silica gel column chromatography (EtOAc /EtOAcCompound 1-1 (205 mg, yield: 52%) was a red liquid.

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Dinuo Pharmaceutical Technology Co., Ltd.; Zhao Zhiming; Gao Daxin; Chen Shoujun; Wu Zhiheng; (105 pag.)CN108623615; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia