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. 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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. name: 6-Chloropyrimidine-4-carbonitrile
The title compound (1-19) was prepared using the procedure for Example 17, using 4- hydroxyindole in Step 1. The free base form of the title compound was purified via silica gel (eluting with 1-20% MeOH in DCM) and then converted to the hydrochloride salt, using 2 M HC1 in ether. ?HNIVIR (300 IVIHz, DMSO-d6): 11.35 (s, 1H), 8.57 (s, 1H), 7.30-7.34 (m, 2H), 7.08 – 7.14 (m, 2H), 6.79 (m, 1H), 6.05 (m, 1H), 3.73 (s, 2H); LCMS Mass: 241.0 (M+1).; A mixture of 6-hydroxyindole 1 (157 mg, 1.18 mmol), 6-chloropyrimidine-4-carbonitrile (150 mg, 1.07 mmol), K2C03 (444 mg, 3.21 mmol), DMF (2 mL), and THF (4 mL), was stirred at RT for 20 h. Additional 6-chloropyrimidine-4-carbonitrile (30 mg, 0.2 15 mmol) was added and the mixture stirred at RT for a further 16 h. The mixture was concentrated under reduced pressure. The residue was purified (silica gel; eluting 0 to 100% EtOAc in hexanes), to afford compound 2 (190 mg, 56%) as a yellow solid. To a stirred solution of compound 2 (40 mg, 0.169 mmol) in EtOAc (3 mL) and HOAc (0.3 mL) at RT, was added 10% Pd/C (10 mol%). The reaction mixture was stirred at RT under hydrogen (1 atmosphere pressure) for 1 h. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated under reduced pressure. The residue was purified via preparative HPLC (Waters XTerra Prep MS C-18 OBD 5 jiM 50 x 100mm column; eluting with 10-90% ACN/H20 containing 0.1% TFA, over 20 mm), followed by silica gel (eluting 0 to 100% EtOAc in hexanes), to afford compound 1-17 (3 mg, 7%) as a solid.
With the rapid development of chemical substances, we look forward to future research findings about 939986-65-9.
Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
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