= 8.6 Hz, 2H), 7.14 (d, J = 5.0 Hz, 1H), 7.03 (s, 1H), six.78(d, J = ten.0 Hz, 2H), 5.24 (s, 2H), five.01 (s, 2H), four.40 (q, J = 7.0 Hz, 1H), three.90 (s, 3H), 2.98 (s, 6H), 2.71 (q, J = 7.six Hz, 2H), 1.53 (d, J = 7.0 Hz, 3H), 1.25 (t, J = six.9 Hz, 3H); 13C NMR (125 MHz, CDCl3) 164.7, 157.9, 156.6, 150.3, 141.9, 129.1, 128.7, 127.9, 119.0, 112.9, 109.two, 103.9, 92.0, 72.three, 55.7, 40.eight, 28.1, 26.9, 22.7, 12.6; IR (neat cm-1) 3310, 3172, 2925, 2873, 1603, 1570, 807; HRMS (ES, M+ + H) m/z 416.2442 (calculated for C25H30N5O, 416.2445). 6-Ethyl-5-[3-(4-fluoro-3-methoxy-biphenyl-4-yl)-but-1-ynyl]-pyrimidine-2,4-diamine (36). According to the common Sonogahisra coupling process ethyl-iodopyrimidine (0.10 g, 0.39 mmol), CuI (0.02 g, 0.08 mmol, 20 mol ), Pd(PPh3)2Cl2 (0.03 g, 0.04 mmol, 10 mol ), and alkyne (0.10 g, 0.39 mmol) have been reacted in DMF/Et3N (1 mL/1 mL) at 60 for 12 h. Just after the mixture was cooled, the dark reddish brown resolution was concentrated, and also the item was purified by flash chromatography (SiO2, ten g, one hundred EtOAc followed by 1 MeOH/CH2Cl2) followed by reverse phase flash chromatography (NH2 capped SiO2, three g, one hundred CH2Cl2) to afford pyrimidine 36 as a off-white solid (0.12 g, 79 ); TLC Rf = 0.26 (five MeOH/CH2Cl2); mp 129.6-130.0 ; 1H NMR (500 MHz, chloroform-d) 7.56-7.50 (m, 3H), 7.13-7.09 (m, 3H), 7.01(s, 1H), 5.30 (br s, 2H), five.19 (br s, 2H) four.41 (q, J = six.9 Hz, 1H), three.91 (s, 3H), 2.73 (q, J = 7.six Hz, 2H), 1.54 (d, J = 7.0 Hz, 3H), 1.27 (t, J = 7.six Hz, 3H). 13C NMR (125 MHz, CDCl3) 164.5, 162.6 (d, J = 245.0 Hz, 1C), 159.five, 156.six, 140.six, 137.three, 130.five, 128.8 (d, J = 7.5 Hz, 2C), 128.1, 119.7, 115.8 (d, J = 21.two Hz, 2C), 109.6, 102.eight, 91.4, 73.7, 55.7, 29.1, 26.9, 22.9, 12.7; IR (neat cm-1) 3463, 3418, 3309, 3164, 2964, 2927, 1621, 1547, 1432, 1219, 1018; HRMS (DART, M++H) m/z 391.1921 (calculated for C23H24FN4O, 391.1934). HPLC (a) tR = 25.five min, 96.8 ; (b) tR = 19.eight min, 97.5 . 5-(3-Biphenyl-4-yl-but-1-ynyl)-6-ethyl-pyrimidine-2,4-diamine (37). As outlined by the common Sonogahisra coupling procedure ethyliodopyrimidine (0.040 g, 0.15 mmol), CuI (0.006 g, 0.03 mmol, 21 mol ), Pd(PPh3)2Cl2 (0.011 g, 0.02 mmol, 10 mol ), and alkyne 27 (0.034 g, 0.17 mmol) had been reacted in DMF/Et3N (1 mL each) at 60 for 12 h. Just after the mixture was cooled, the dark reddish brown solution was concentrated, and also the solution was purified by flash chromatography (SiO2, 5 g, 2 MeOH/CHCl3) to afford coupled pyrimidine 37 as a pale white powder (0.Olsalazine 040 g, 77 ) followed by reverse phase flash chromatography (NH2 capped SiO2, 3 g, 100 CH2Cl2) for biological evaluation: TLC Rf = 0.AAA 1 (five MeOH/ CH2Cl2); mp 129.PMID:25046520 3-131.1 ; 1H NMR (500 MHz, CDCl3) 7.59- 7.55 (m, 4H), 7.48 (d, J = eight. Hz, 2H), 7.42 (dd, J = 7.6, 7.6 Hz, 2H), 7.42 (dd, J = 7.6, 7.six Hz, 1H), 7.36-7.30 (m, 1H), 5.13 (s, 2H), 4.87 (s, 2H), four.07 (q, J = 7.1 Hz, 1H), 2.69 (q, J = 7.6 Hz, 2H), 1.61 (d, J = 7.1 Hz, 3H), 1.23 (t, J = 7.6 Hz, 3H); 13C NMR (125 MHz, CDCl3) 173.7, 164.five, 160.9, 142.6, 140.9, 140.0, 128.9, 127.six, 127.five, 127.4, 127.3, 101.8, 90.eight, 75.six, 32.9, 29.9, 24.9, 12.eight; IR (neat cm-1) 3415, 3304, 3162, 2973, 2927, 2871, 1618, 1547, 1436, 1281, 761, 692, 479; HRMS (ESI, M+ + H) m/z 343.1907 (calculated for C22H23N4, 343.1917). HPLC (a) tR = 19.1 min, 98.9 ; (b) tR = 17.three min, 98.five . 6-Ethyl-5-[3-(6-phenyl-pyridin-3-yl)-but-1-ynyl]-pyrimidine-2,4diamine (46). According to the basic Sonogahisra coupling process, ethyl-iodopyrimidine (0.071 g, 0.27 mmol), CuI (0.dx.doi.org/10.1021/jm40.
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