Application of 939986-65-9 , The common heterocyclic compound, 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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 a suspension of (S)-(5 -(3,5 -difluorophenyl)-4,5-dihydro- 1H-pyrazol- 1 -yl)(piperidin-4- yl)methanone, 1R-(-)-camphor-10-sulphonic acid salt (300 mg, 0.57 mmol) in MeCN (30mL) was added 6-chloropyrimindine-4-carbonitrile (80 mg, 0.57 mmol) and DIPEA (0.25 mL,1.43 mmol) The vessel was sealed and heated at 80C for 2 h. The reaction minxture was evaporated in vacuo. This residue was purified by normal phase column chromatography [CyHI(EtOAc/EtOH 3:1) 100/0 to 70/301. A trituration into iPr2O afforded, after filtration, (S)-6-(4-(5 -(3 ,5-difluorophenyl)-4,5 -dihydro- 1H-pyrazole- 1 -carbonyl)piperidin- 1-yl)pyrimindine-4-carbonitrile (130 mg, 0.33 mmol, purity: 100 %, recovery: 58 %) as a light yellow powder. LCMS (m/z) 397 (M+H), retention time: 2.48 min LC/MS Method 1. ?H NMR (400 min-Tz, DMSO-d6) delta ppm 8.54 (s, 1H), 7.57 (s, 1H), 7.26 (s, 1H), 7.12 (tt, J9.4, 2.1 Hz, 1H), 6.84 (d, J=6.5 Hz, 2H), 5.34 (dd, J=12.0, 4.9 Hz, 1H), 4.47 (br.s, 2H), 3.49 (ddd, J=19.0, 12.0, 1.0 Hz, 1H), 3.43 (tt, J=11.4, 3.7 Hz, 1H), 3.13 (brs, 2H), 2.75 (ddd, J19.2,4.9, 1.5 Hz, 1H), 1.95 (d, J=12.7 Hz, 1H), 1.81 (d, J=12.7 Hz, 1H), 1.48 (m, 2H).
The synthetic route of 939986-65-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; (243 pag.)WO2018/92089; (2018); A1;,
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