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MedChemComm
Page 10 of 15
DOI: 10.1039/C6MD00447D
ARTICLE
Journal Name
1
(6f). Yellow solid, Yield 81%, mp 239-241 °C; IR (neat): 3611, 722 cm-1; H NMR (400 MHz, DMSO-d6) δ 11.70 (s, 1H), 10.23
1
3389, 2937, 1730, 1618, 712 cm-1; H NMR (400 MHz, DMSO- (s, 1H), 9.20 (s, 1H), 8.36 (s, 1H), 7.71 (s, 1H), 7.55 (d, J = 8.8 Hz,
d6) δ 11.49 (s, 1H), 10.39 (s, 1H), 9.17 (s, 1H), 9.08 (s, 1H), 8.21 2H), 7.43 (d, J = 8.8 Hz, 2H), 7.25 (d, J = 1.9 Hz, 1H), 7.06 (d, J =
(s, 1H), 7.68 (s, 1H), 7.24 (t, J = 2.1 Hz, 1H), 7.22 – 7.18 (m, 2H), 1.9 Hz, 1H), 5.12 (d, J = 3.0 Hz, 1H), 4.02 – 3.99 (m, 2H), 2.25 (s,
7.06 – 7.03 (m, 2H), 6.61 – 6.58 (m, 1H), 5.11 (d, J = 3.1 Hz, 1H), 3H), 1.38 (s, 9H), 1.12 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz,
4.03 – 3.97 (m, 2H), 3.75 (s, 3H), 2.26 (s, 3H), 1.39 (s, 9H), 1.12 DMSO-d6): 165.9, 155.1, 152.7, 148.7, 148.5, 138.7, 137.1,
(t, J = 7.1 Hz, 3H); 13C NMR (DMSO-d6, 100 MHz): 165.4, 159.6, 136.2, 129.8, 128.6, 127.6, 118.4, 99.9, 59.7, 53.9, 34.9, 29.7,
155.5, 152.2, 151.9, 148.0, 145.7, 140.5, 136.2, 135.3, 129.4, 18.2, 14.6; HRMS (ESI) calcd for C26H30ClN5O4S [M + H]+
126.2, 126.0, 118.1, 111.4, 107.8, 104.8, 99.5, 59.1, 54.9, 53.6, 544.1780, found 544.1772.
34.4, 29.2, 17.7, 14.1; HRMS (ESI) calcd for C27H33N5O6 [M + H]+
524.2504, found 524.2472.
ethyl
(E)-4-(3-(tert-butyl)-4-hydroxy-5-((2-
(methylcarbamothioyl)hydrazono)methyl)phenyl)-6-methyl-
ethyl
(E)-4-(3-(tert-butyl)-5-((2-((4- 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (6k). White
fluorophenyl)carbamoyl)hydrazono)methyl)-4-
solid, Yield 77%, mp 196-198 °C; IR (neat): 3711, 3431, 2974,
1744, 1632, 752 cm-1; 1H NMR (400 MHz, DMSO- d6) δ 11.30 (s,
hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-
tetrahydropyrimidine-5-carboxylate (6g). White solid , Yield 1H), 9.97 (s, 1H), 9.19 (d, J = 1.5 Hz, 1H), 8.46 (d, J = 4.4 Hz,
84%, mp 242-244 °C; IR (neat): 3677, 3406, 2936, 1744, 1666, 1H), 8.26 (s, 1H), 7.69 (d, J = 2.7 Hz, 1H), 7.22 (d, J = 2.0 Hz,
730 cm-1; 1H NMR (400 MHz, DMSO-d6) δ 11.80 (s, 1H), 9.97 (s, 1H), 6.99 (d, J = 2.1 Hz, 1H), 5.11 (d, J = 3.2 Hz, 1H), 4.02 -3.99
1H), 9.23 (s, 1H), 8.83 (s, 1H), 8.00 (s, 1H), 7.74 (s, 1H), 7.54 – (m, 2H), 3.02 (d, J = 4.4 Hz, 3H), 2.25 (s, 3H), 1.39 (s, 9H), 1.12
7.50 (m, 3H), 7.44 (d, J = 2.2 Hz, 1H), 7.09 (t, J = 8.9 Hz, 2H), (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, DMSO-d6): 177.8, 165.8,
5.16 (d, J = 3.2 Hz, 1H), 4.00 (q, J = 6.8 Hz, 2H), 2.27 (s, 3H), 154.8, 152.7, 148.6, 147.5, 136.9, 136.2, 127.6, 127.2, 118.3,
1.37 (s, 9H), 1.10 (t, J = 7.1 Hz, 3H); 13C NMR (DMSO-d6, 100 99.9, 59.7, 53.9, 34.9, 31.7, 29.7, 18.2, 14.6; HRMS (ESI) calcd
MHz): 199.0, 165.7, 159.6, 159.0, 156.7, 152.4, 149.1, 137.6, for C21H29N5O4S [M + H]+ 448.2013, found 448.2046.
136.6, 133.1, 129.6, 120.9, 120.8, 115.6, 115.4, 99.4, 59.7,
ethyl
(E)-4-(3-(tert-butyl)-5-((2-
54.0, 34.8, 29.5, 18.3, 14.6; HRMS (ESI) calcd for C26H30FN5O5 carbamoylhydrazono)methyl)-4-hydroxyphenyl)-6-methyl-2-
[M + H]+ 512.2304, found 512.2311
oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (6l). White
ethyl
(E)-4-(3-((2-((4- solid, Yield 81%, mp 185-187 °C; IR (neat): 3701, 3445, 2917,
1
bromophenyl)carbamoyl)hydrazono)methyl)-5-(tert-butyl)-4- 1751, 1674, 756 cm-1; H NMR (400 MHz, DMSO) δ 11.12 (s,
hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-
1H), 10.17 (s, 1H), 9.16 (d, J = 1.6 Hz, 1H), 8.06 (s, 1H), 7.72 –
tetrahydropyrimidine-5-carboxylate (6h). White solid, Yield 7.63 (m, 1H), 7.17 (d, J = 2.1 Hz, 1H), 6.96 (d, J = 2.1 Hz, 1H),
78%, mp 277-279 °C; IR (neat): 3701, 3478, 2947, 1695, 1580, 6.37 (s, 2H), 5.09 (d, J = 3.2 Hz, 1H), 4.04 – 3.96 (m, 2H), 2.25
1
789 cm-1; H NMR (400 MHz, DMSO-d6) δ 11.32 (s, 1H), 10.50 (s, 3H), 1.38 (s, 9H), 1.11 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz,
(s, 1H), 9.26 (s, 1H), 9.17 (s, 1H), 8.21 (s, 1H), 7.68 (s, 1H), 7.53 DMSO-d6): 165.9, 155.9, 155.2, 152.7, 148.5, 144.7, 136.5,
(d, J = 9.0 Hz, 2H), 7.47 (d, J = 8.9 Hz, 2H), 7.20 (d, J = 1.7 Hz, 135.7, 126.4, 126.3, 118.6, 100.0, 59.6, 54.0, 49.0, 34.9, 29.7,
1H), 7.03 (d, J = 1.7 Hz, 1H), 5.11 (d, J = 3.0 Hz, 1H), 4.02 - 3.98 18.2, 14.6; HRMS (ESI) calcd for C20H27N5O5 [M + H]+ 418.2085,
(m, 2H), 2.26 (s, 3H), 1.39 (s, 9H), 1.12 (t, J = 7.1 Hz, 3H); 13C found 418.2087.
NMR (100 MHz, DMSO-d6): 165.8, 155.4, 152.6, 152.4, 148.5,
ethyl
(E)-4-(3-(tert-butyl)-5-((2-
146.4, 139.2, 136.6, 135.8, 131.8, 126.7, 126.6, 121.5, 118.4, carbamothioylhydrazono)methyl)-4-hydroxyphenyl)-6-
114.3, 99.9, 59.6, 54.1, 34.9, 29.7, 18.2, 14.6; HRMS (ESI) calcd methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
for C26H30BrN5O5 [M + H]+ 572.1503, found 572.1527.
ethyl
(phenylcarbamothioyl)hydrazono)methyl)phenyl)-6-methyl-
(6m). White solid, yield: 79%; mp 225-227 °C; IR(neat): 3709,
(E)-4-(3-(tert-butyl)-4-hydroxy-5-((2- 3455, 2935, 1745, 1674, 711 cm-1; 1H NMR (DMSO-d6, 400
MHz): δ 11.30 (s, 1H), 9.90 (s, 1H), 9.19 (d, J =1.6 Hz, 1H), 8.24
2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (6i). White (s, 1H), 8.04 (bs, 2H), 7.69 (m, 3H), 7.22 (d, J =2.12 Hz, 1H),
solid, Yield 81%, mp 237-239 °C; IR (neat): 3688, 3512, 2978, 7.00 (d, J =2.4 Hz, 3H), 5.11 (d, J =3.2 Hz, 1H), 4.02-3.99 (m,
1745, 1692, 689 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 11.62 (s, 2H), 2.24 (s, 3H), 1.37(s, 9H), 1.12 (t, J = 7.1 Hz, 3H), 13C NMR
1H), 10.18 (s, 1H), 9.20 (s, 1H), 8.36 (s, 1H), 7.71 (s, 1H), 7.51 (DMSO-d6, 75 MHz): δ 165.8, 155.0, 152.6, 148.5, 147.6, 136.9,
(d, J = 7.7 Hz, 2H), 7.38 (t, J = 7.5 Hz, 2H), 7.24 (s, 1H), 7.21 (t, J 136.1, 127.4, 127.2, 118.3, 99.9, 79.6, 59.6, 53.9, 40.5, 40.3,
= 7.2 Hz, 1H), 7.06 (s, 1H), 5.12 (d, J = 3.0 Hz, 1H), 4.04 – 3.99 40.1, 39.9, 39.7, 39.5, 39.3, 34.9, 29.6, 18.2, 14.6; HRMS (ESI)
(m, 2H), 2.25 (s, 3H), 1.38 (s, 9H), 1.12 (t, J = 6.8 Hz, 3H); 13C calcd for C20H27N5O4S [M + H]+ 434.1857, found 434.1864.
NMR (100 MHz, DMSO-d6): 165.9, 155.0, 152.7, 148.6, 148.1,
ethyl
(E)-4-(3-((2-((4-
139.7, 137.1, 136.2, 128.7, 127.5, 127.4, 126.0, 125.8, 118.5, chlorophenyl)carbamoyl)hydrazono)methyl)-4-hydroxy-5-
99.9, 59.7, 53.9, 35.0, 29.7, 18.2, 14.6; HRMS (ESI) calcd for methylphenyl)-6-methyl-2-thioxo-1,2,3,4-
C26H31N5O4S [M + H]+ 510.2170, found 510.2173.
ethyl
tetrahydropyrimidine-5-carboxylate (6n). White solid, Yield
(E)-4-(3-(tert-butyl)-5-((2-((4- 85%, mp 241-243 °C; IR (neat): 3688, 3478, 2944, 1741, 1625,
1
chlorophenyl)carbamothioyl)hydrazono)methyl)-4-
hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-
742 cm-1; H NMR (400 MHz, DMSO-d6) δ 10.61 (s, 1H), 10.29
(s, 1H), 9.59 (s, 1H), 9.14 (s, 1H), 8.21 (s, 1H), 7.60 (d, J = 8.9 Hz,
tetrahydropyrimidine-5-carboxylate (6j). White solid, Yield 2H), 7.35 (d, J = 8.8 Hz, 2H), 7.14 (d, J = 1.8 Hz, 1H), 7.01 (d, J =
79%, mp 213-215 °C; IR (neat): 3704, 3512, 2959, 1733, 1698, 1.7 Hz, 1H), 5.13 (d, J = 3.5 Hz, 1H), 4.04-4.01 (m, 2H), 2.30 (s,
10 | J. Name., 2012, 00, 1-3
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