RSC Advances
Paper
138 mg of 4-nitroaniline and puried by column chromatog-
raphy starting from hexane to hexane–ethyl acetate (8 : 2) as the
eluent.
4,6-Dimethyl-N-(4-methylphenyl)-2-pyrimidinamine
(5).
Yield ¼ 99%; brown solid; mp 116–117 ꢀC. It was obtained from
107 mg of 4-toluidine and puried by column chromatography
starting from hexane to hexane–ethyl acetate (9 : 1) as the
eluent.
1
IR (KBr) nmax cmꢁ1 3383, 2985, 1600, 1564, 1541, 1506; H-
NMR (CDCl3): d 2.49 (s, 6H, 2CH3), 6.68 (s, 1H, Ar Pyr), 7.86
(d, J ¼ 8.7, 2H, Ar), 8.21 (d, J ¼ 8.7, 2H, Ar), 8.70 (s, 1H, NH); 13C-
NMR (CDCl3): d 23.7, 113.3, 118.5, 125.4, 142.4, 144.9, 156.9,
168.1; ESI-HRMS [M + H]+ found ¼ 245.10289, C12H13N4O2
requires ¼ 245.10330.
IR (KBr) nmax cmꢁ1 3263, 2964, 1609, 1585, 1565, 1541; H-
1
NMR (CDCl3): d 2.31 (s, 3H, CH3), 2.35 (s, 6H, 2CH3), 6.45 (s,
1H, Ar Pyr), 7.12 (d, J ¼ 8.1, 2H, Ar), 7.43 (s, 1H, NH), 7.54 (d, J ¼
8.1, 2H, Ar); 13C-NMR (CDCl3): d 20.8, 23.9, 111.3, 119.2, 129.4,
131.6, 137.3, 159.8, 167.6; ESI-HRMS [M + H]+ found ¼
214.13349, C13H16N3 requires ¼ 214.13387.
N-(Biphenyl-4-yl)-4,6-dimethyl-2-pyrimidinamine (11). Yield
¼ 91%; light brown solid; mp 114–115.5 ꢀC. It was obtained
from 169 mg of 4-aminobiphenyl and puried by column
chromatography starting from CH2Cl2–hexane (2 : 8), to CH2Cl2
as the eluent.
N-(4-Bromophenyl)-4,6-dimethyl-2-pyrimidinamine
(6).
Yield ¼ 98%; white solid; mp 123–124 ꢀC. It was obtained from
172 mg of 4-bromoaniline and puried by column chromatog-
raphy starting from CH2Cl2 to CH2Cl2–isopropanol (95 : 5) as
the eluent.
1
IR (KBr) nmax cmꢁ1 3242, 2962, 1602, 1573, 1561, 1534; H-
NMR (CDCl3): d 2.41 (s, 6H, 2CH3), 6.50 (s, 1H, Ar Pyr), 7.31–
7.36 (m, 1H, Ar), 7.43–7.48 (m, 2H, Ar), 7.58–7.64 (m, 4H, Ar, s,
1H, NH), 7.78–7.82 (m, 2H, Ar), 13C-NMR (CDCl3): d 23.9, 111.7,
119.2, 126.7, 127.5, 128.8, 134.8, 139.4, 140.9, 159.6, 167.6; ESI-
HRMS [M + H]+ found ¼ 276.14892, C18H18N3 requires ¼
276.14952.
IR (KBr) nmax cmꢁ1 3408, 2962, 1595, 1564, 1519; 1H-NMR
(CDCl3): d 2.33 (s, 6H, 2CH3), 6.47 (s, 1H, Ar Pyr), 7.36 (d, J ¼
8.7, 2H, Ar), 7.54 (d, J ¼ 8.7, 2H, Ar), 7.67 (s, 1H, NH); 13C-NMR
(CDCl3): d 23.9, 111.9, 114.1, 120.4, 131.6, 139.1, 159.4, 167.6;
ESI-HRMS [M + H]+ found ¼ 278.02861, C12H13BrN3 requires ¼
278.02874.
4,6-Dimethyl-N-{4-[(E)-phenyldiazenyl]-phenyl}-2-pyrimidinamine
(12). Yield ¼ 91%; red solid; mp 159.5–161 ꢀC. It was obtained from
197 mg of 4-aminobenzene and puried by column chromatography
using hexane–ethyl acetate (9 : 1) as the eluent.
N-(4-Chlorophenyl)-4,6-dimethyl-2-pyrimidinamine
(7).
Yield ¼ 82%; brown solid; mp 118–120 ꢀC. It was obtained from
128 mg of 4-chloroaniline and puried by column chromatog-
raphy starting from CH2Cl2 to CH2Cl2–isopropanol (98 : 2) as
the eluent.
1
IR (KBr) nmax cmꢁ1 3278, 2960, 1604, 1585, 1562, 1535; H-
NMR (CDCl3): d 2.39 (s, 6H, 2CH3), 6.52 (s, 1H, Ar Pyr), 7.39–
7.52 (m, 3H, Ar), 7.83–7.96 (m, 7H, Ar, NH); 13C-NMR (CDCl3):
d 23.9, 112.5, 118.5, 122.6, 124.2, 129.1, 130.3, 142.9, 147.5,
152.9, 159.1, 167.7; ESI-HRMS [M + H]+ found ¼ 304.15492,
IR (KBr) nmax cmꢁ1 3317, 2949, 1612, 1593, 1544,; H-NMR
1
(acetone d6): d 2.31 (s, 6H, 2CH3), 6.59 (s, 1H, Ar Pyr), 7.29 (d,
J ¼ 8.8, 2H, Ar), 7.95 (d, J ¼ 8.8, 2H, Ar), 8.59 (s, 1H, NH); 13C-
NMR (acetone d6): d 23.9, 112.2, 120.9, 126.1, 129.1, 140.9,
C
18H18N5 requires ¼ 304.15567.
160.7, 168.2; ESI-HRMS [M
12H13ClN3 requires ¼ 234.07925.
N-(4-Fluorophenyl)-4,6-dimethyl-2-pyrimidinamine (8). Yield
+
H]+ found
¼
234.07884,
{3-[(4,6-Dimethylpyrimidine-2-yl)-amino]-phenyl}-methanol
(13). Yield ¼ 97%; yellow solid; mp 106–108 ꢀC. It was obtained
from 123 mg of 3-aminobenzyl alcohol and puried by column
chromatography starting from hexane to hexane–ethyl acetate
(1 : 1) as the eluent.
C
¼ 71%; brown solid; mp 91–93 ꢀC. It was obtained from 111 mg
of 4-uoroaniline and puried by column chromatography
starting from CH2Cl2 to CH2Cl2–isopropanol (98 : 2) as the
eluent.
1
IR (KBr) nmax cmꢁ1 3271, 2939, 1618, 1593, 1556, 1548; H-
NMR (CDCl3): d 2.32 (s, 6H, 2CH3), 3.73 (bs, 1H, OH), 4.62 (s,
2H, CH2), 6.43 (s, 1H, Ar Pyr), 6.93–6.95 (m, 1H, Ar), 7.19–7.25
(m, 1H, Ar), 7.37 (s, 1H, NH), 7.49 (bs, 1H, Ar), 7.58–7.61 (m, 1H,
Ar); 13C-NMR (CDCl3): d 23.8, 64.8, 111.6, 117.5, 118.1, 120.7,
128.9, 139.9, 141.9, 159.4, 167.6; ESI-HRMS [M + H]+ found ¼
230.12849, C13H16N3O requires ¼ 230.12879.
IR (KBr) nmax cmꢁ1 3267, 2964, 1614, 1595, 1566, 1550; H-
1
NMR (CDCl3): d 2.34 (s, 6H, 2CH3), 6.47 (s, 1H, Ar Pyr), 6.95–
7.01 (m, 2H, Ar), 7.48 (s, 1H, NH), 7.56–7.60 (m, 2H, Ar); 13C-
NMR (CDCl3): d 23.8, 111.6, 115.3 (d, J ¼ 22), 120.6 (d, J ¼
6.7), 135.8, 158.3 (d, J ¼ 242), 159.4, 167.6; ESI-HRMS [M + H]+
found ¼ 218.10849, C12H13FN3 requires ¼ 218.10880.
N-(3-Fluorophenyl)-4,6-dimethyl-2-pyrimidinamine
(14).
Yield ¼ 97%; white solid; mp 132–134 ꢀC. It was obtained from
111 mg of 3-uoroaniline and puried by column chromatog-
raphy starting from CH2Cl2 to CH2Cl2–isopropanol (95 : 5) as
the eluent.
4,6-Dimethyl-N-[4-(triuoromethyl)phenyl]-2-pyrimidinamine
(9). Yield ¼ 87%; yellow solid; mp 106.5–108 ꢀC. It was obtained
from 161 mg of 4-triuoromethylaniline and puried by column
chromatography using hexane–ethyl acetate (9 : 1) as the eluent.
1
IR (KBr) nmax cmꢁ1 3419, 2922, 1602, 1587, 1566, 1539; H-
1
IR (KBr) nmax cm-1 3435, 2989, 1618, 1600, 1598, 1535; H-
NMR (CDCl3): d 2.37 (s, 6H, 2CH3), 6.51 (s, 1H, Ar Pyr), 6.63–
6.71 (m, 1H, Ar), 7.12–7.24 (m, 2H, Ar), 7.62 (s, 1H, NH), 7.78–
7.83 (m, 1H, Ar); 13C-NMR (CDCl3): d 23.9, 105.9 (d, J ¼ 27.0),
108.5 (d, J ¼ 22), 112.2, 114.1 (d, J ¼ 2.5), 129.8 (d, J ¼ 9.9), 141.7
(d, J ¼ 5.8), 159.4, 163.3 (d, J ¼ 242), 167.7; ESI-HRMS [M + H]+
found ¼ 218.10851, C12H13FN3 requires ¼ 218.10880.
NMR (CDCl3): d 2.39 (s, 6H, 2CH3), 6.55 (s, 1H, Ar Pyr), 7.53
(d, J ¼ 8.4, 2H, Ar), 7.73 (s, 1H, NH), 7.78 (d, J ¼ 8.4, 2H, Ar); 13C-
NMR (CDCl3): d 23.9, 112.5, 118.1, 122.5, 126.1, 143.1, 159.2,
167.8; ESI-HRMS [M + H]+ found ¼ 268.10489, C13H13F3N3
requires ¼ 268.10561.
4,6-Dimethyl-N-(4-nitrophenyl)-2-pyrimidinamine (10). Yield
¼ 39%; yellow solid; mp 221–223 ꢀC. It was obtained from
3-[(4,6-Dimethylpyrimidine-2-yl)-amino]-phenol (15). Yield
¼ 85%; brown solid; mp 137.5–139 ꢀC. It was obtained from
12252 | RSC Adv., 2020, 10, 12249–12254
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