Related Products 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.
In a pre-dried thumb flask, 59-1 (0.8 g, 3.42 mmol), I1 (690.72 mg, 3.11 mmol), cuprous iodide (591.84 mg, 3.11 mmol), potassium carbonate (588.42 mg, 4.26 mmol) N,N’-dimethylethylenediamine (301.33 mg, 3.42 mmol, 367.92 muL,) and 1,4-dioxane (20 mL) were added in sequence, the reaction mixture was replaced by nitrogen for 3 times, then heated and stirred in an oil bath at 95C for 13 hours. For another batch, 59-1 (200.85 mg, 858.21 mumol), I1 (190.75 mg, 858.21 mumol), cuprous iodide (163.45 mg, 858.21 mumol), potassium carbonate (162.50 mg, 1.18 mmol), N,N’-dimethylethylenediamine (83.22 mg, 944.04 mumol, 101.61 muL) and 1,4-dioxane (5 mL) were added sequentially in a pre-dried thumb flask, the reaction mixture was replaced by nitrogen for 3 times, then heated and stirred in an oil bath at 95C for 13 hours. Half of the reaction mixture and previous batch of the reaction mixture were combined and directly evaporated. The residue was purified by a silica gel column (100-200 mesh silica gel, PE_EA=5/1-0/1) to give 0.7 g pale brown oily product. 0.5 g of the oily product was added into 20 mL water, then extracted by 60 mL DCM for 3 times, the organic phase was dried, then filtered and evaporated to dry. The residue was purified by a silica gel column (100-200 mesh silica gel, PE_EA=5/1-0/1) to give 59-2. 1H NMR (400 MHz, CDCl3): 8.97 (s, 1H), 8.09-8.06 (m, 1H), 7.70-7.43 (m, 2 H), 5.71-5.64 (m, 1H), 5.07-5.05 (d, J=10.4 Hz, 1H), 4.93-4.88 (m, 1H), 4.81-4.79 (d, J=6.4 Hz, 2H), 2.61 (s, 3H), 1.81-1.75 (m, 6H)
The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.
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