Synthetic Route of 18740-39-1, 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.18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine, molecular formula is C6H2Cl2N2S, molecular weight is 205.0645, as common compound, the synthetic route is as follows.
To a solution of 2,4-dichlorothieno[2,3-d]pyrimidine (200 mg, 975.31 umol, 1 eq) in i-PrOH (15 mL) was added DIPEA (630.24 mg, 4.88 mmol, 849.38 uL, 5.0 eq) and 2-(lH-indol-3- yl)ethanamine (203.14 mg, 1.27 mmol, 1.3 eq). The mixture was stirred at 50 °C for 3 h. LC-MS showed the starting material was consumed completely and one main peak with desired MS was detected. The reaction mixture was diluted with H2O (15 mL) and extracted with DCM (15 mL x 3). The combined organic layers were dried over Na2S04 filtered and concentrated under reduced pressure to give a residue which was purified by flash silica gel chromatography (ISCO®; 12 g SepaFlash® Silica Flash Column, Eluent of 20-30percent EtOAc/PE gradient (at) 50 mL/min) to give 2-chloro-N-[2-(lH-indol-3-yl)ethyl]thieno[2,3-d]pyrimidin-4-amine (260 mg, 774.90 umol, 79.4percent yield) as a yellow solid. NMR (400 MHz, CD3OD) delta ppm 7.67 (d, J= 7.9 Hz, 1H), 7.40- 7.35 (m, 2H), 7.31 (d, J = 8.2 Hz, 1H), 7.10-7.05 (m, 2H), 7.00-6.93 (m, 1H), 3.86-3.79 (m, 2H), 3.11 (t, J= 7.4 Hz, 2H); ES-LCMS m/z 329.0, 331.0 [M+H]
The chemical industry reduces the impact on the environment during synthesis 18740-39-1, I believe this compound will play a more active role in future production and life.
Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia