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5.1.29. 2-{[2-(4-Iodophenyl)-6-methylpyrimidin-4-
yl]amino}ethanol oxalate (9d)
5.1.38. 2-{[2-(4-Bromophenyl)-6-methylpyrimidin-4-
yl](methyl)amino}ethanol hydrochloride (9m)
White solid (yield 84%); 1H NMR (DMSO-d6) d 2.29 (3H, s), 3.20–
3.70 (4H, m), 6.33 (1H, s), 7.10–7.70 (1H, br), 7.84 (2H, d,
J = 8.3 Hz), 8.08 (2H, d, J = 8.3 Hz); FAB-MS m/z 356 [(M+H)+]. Anal.
(C13H14N3OIꢁC2H2O4ꢁ0.25H2O): C, H, N, I.
White solid (yield 12%); 1H NMR (DMSO-d6) d 2.48 (3H, s), 3.20–
3.40 (3H, m), 3.60–4.00 (4H, m), 6.75–7.15 (1H, br), 7.85 (2H, d,
J = 8.4 Hz), 8.19 (2H, d, J = 8.4 Hz); FAB-MS m/z 322, 324
[(M+H)+]. Anal. (C14H16N3OBrꢁHClꢁ0.3H2O): C, H, N, Br, Cl.
5.1.30. 2-{[2-(4-Methoxyphenyl)-6-methylpyrimidin-4-
yl]amino}ethanol (9e)
5.1.39. 2-{[2-(4-Bromophenyl)-6-methylpyrimidin-4-
yl]amino}propan-1-ol oxalate (9n)
White solid (yield 68%); 1H NMR (CDCl3) d 2.39 (3H, s), 3.60–
3.64 (2H, m), 3.84 (2H, t, J = 4.9 Hz), 3.85 (3H, s), 5.14 (1H, s),
6.09 (1H, s), 6.93–6.97 (2H, m), 8.27–8.30 (2H, m); FAB-MS m/z
260 [(M+H)+]. Anal. (C14H17N3O2): C, H, N.
White solid (yield 22%); 1H NMR (DMSO-d6) d 1.16 (3H, d,
J = 6.8 Hz), 2.29 (3H, s), 3.38 (1H, dd, J = 5.9, 10.8 Hz), 3.50 (1H,
dd, J = 5.4, 10.8 Hz), 3.80–4.50 (2H, m), 6.31 (1H, s), 7.29 (1H, s),
7.67 (2H, d, J = 8.7 Hz), 8.23 (2H, d, J = 8.7 Hz); FAB-MS m/z 322,
324 [(M+H)+]. Anal. (C14H16N3OBrꢁC2H2O4): C, H, N, Br.
5.1.31. 2-{[6-Methyl-2-(4-methylphenyl)pyrimidin-4-
yl]amino}ethanol (9f)
5.1.40. 1-{[2-(4-Bromophenyl)-6-methylpyrimidin-4-
yl]amino}propan-2-ol oxalate (9o)
White solid (yield 82%); 1H NMR (CDCl3) d 2.37 (3H, s), 2.38 (3H,
s), 3.50–3.55 (2H, m), 3.79 (2H, t, J = 4.9 Hz), 5.27 (1H, s), 6.06 (1H,
s), 7.23 (2H, d, J = 7.8 Hz), 8.19 (2H, d, J = 7.8 Hz); FAB-MS m/z 244
[(M+H)+]. Anal. (C14H17N3O): C, H, N.
White solid (yield 34%); 1H NMR (DMSO-d6) d 1.11 (3H, d,
J = 6.3 Hz), 2.29 (3H, s), 2.80–3.70 (2H, m), 3.83 (1H, q, J = 6.0 Hz),
6.36 (1H, s), 7.20–7.60 (1H, br), 7.67 (2H, d, J = 8.8 Hz), 8.24 (2H,
d, J = 8.8 Hz); FAB-MS m/z 322, 324 [(M+H)+]. Anal. (C14H16N3OBrꢁ-
C2H2O4): C, H, N, Br.
5.1.32. 2-{[2-(4-Bromophenyl)pyrimidin-4-yl]amino}ethanol
oxalate (9g)
Pale yellow solid (yield 58%); 1H NMR (DMSO-d6) d 3.30–3.70
(4H, m), 6.49 (1H, d, J = 5.8 Hz), 7.55–7.70 (1H, br), 7.67 (2H, d,
J = 8.8 Hz), 8.80–8.20 (1H, m), 8.24 (2H, d, J = 8.8 Hz); FAB-MS m/z
294, 296 [(M+H)+]. Anal. (C12H12N3OBrꢁC2H2O4ꢁ0.25H2O): C, H, N,
Br.
5.1.41. 2-(4-Bromophenyl)-N-(2-methoxyethyl)-6-
methylpyrimidin-4-amine oxalate (9p)
White solid (yield 17%); 1H NMR (DMSO-d6) d 2.30 (3H, s), 3.29
(3H, s), 3.51 (2H, t, J = 4.9 Hz), 3.53–3.80 (2H, m), 6.35 (1H, s),
7.40–7.70 (1H, br), 7.68 (2H, d, J = 8.3 Hz), 8.24 (2H, d, J = 8.3 Hz);
FAB-MS m/z 322, 324 [(M+H)+]. Anal. (C14H16N3OBrꢁ-
C2H2O4ꢁ0.75H2O): C, H, N, Br.
5.1.33. 2-{[2-(4-Bromophenyl)-6-ethylpyrimidin-4-
yl]amino}ethanol (9h)
Pale brown solid (yield 94%); 1H NMR (CDCl3) d 1.21 (3H, t,
J = 7.5 Hz), 2.55 (2H, q, J = 7.5 Hz), 3.44–3.52 (2H, m), 3.54–3.60
(2H, m), 4.75 (1H, t, J = 5.4 Hz), 6.31 (1H, s), 7.25–7.40 (1H, br),
7.65 (2H, d, J = 8.6 Hz), 8.26 (2H, d, J = 8.6 Hz); FAB-MS m/z 322,
324 [(M+H)+]. Anal. (C14H16N3OBr): C, H, N, Br.
5.1.42. 2-(4-Bromophenyl)-N-isobutyl-6-methylpyrimidin-4-
amine oxalate (9q)
White solid (yield 57%); 1H NMR (DMSO-d6) d 0.93 (6H, d,
J = 6.3 Hz), 1.80–2.00 (1H, m), 2.28 (3H, s), 2.70–4.50 (2H, m),
6.31 (1H, s), 7.40–7.60 (1H, br), 7.67 (2H, d, J = 8.3 Hz), 8.23 (2H,
d, J = 8.3 Hz); FAB-MS m/z 320, 322 [(M+H)+]. Anal.
(C15H18N3BrꢁC2H2O4): C, H, N, Br.
5.1.34. 2-{[2-(4-Bromophenyl)-6-difluoromethylpyrimidin-4-
yl]amino}ethanol oxalate (9i)
White solid (yield 34%); 1H NMR (DMSO-d6) d 2.80–4.00 (5H,
m), 6.71 (1H, s), 6.79 (1H, t, J = 54.7 Hz), 7.70 (2H, d, J = 8.3 Hz),
7.97 (1H, s), 8.26 (2H, d, J = 8.3 Hz); FAB-MS m/z 344, 346
[(M+H)+]. Anal. (C13H12N3OBrF2ꢁC2H2O4): C, H, N, Br, F.
5.1.43. 2-(4-Bromophenyl)-6-methyl-N-(pyridin-3-
ylmethyl)pyrimidin-4-amine oxalate (9r)
White solid (yield 64%); 1H NMR (DMSO-d6) d 2.30 (3H, s), 4.50–
4.80 (2H, m), 6.36 (1H, s), 7.36 (1H, dd, J = 4.8, 7.9 Hz), 7.64 (2H, d,
J = 8.3 Hz), 7.77 (1H, d, J = 7.9 Hz), 7.95–8.01 (1H, m), 8.23 (2H, d,
J = 8.3 Hz), 8.45 (1H, d, J = 3.6 Hz), 8.62 (1H, s); FAB-MS m/z 355,
357 [(M+H)+]. Anal. (C17H15N3Brꢁ2C2H2O4ꢁH2O): C, H, N, Br.
5.1.35. 2-{[2-(4-Bromophenyl)-6-trifluoromethylpyrimidin-4-
yl]amino}ethanol (9j)
Pale brown solid (yield 93%); 1H NMR (DMSO-d6) d 3.50–3.68
(4H, m), 4.84 (1H, t, J = 5.2 Hz), 6.89 (1H, s), 7.71 (2H, d,
J = 8.6 Hz), 8.14–8.23 (1H, m), 8.26 (2H, d, J = 8.6 Hz); FAB-MS m/
z 362, 364 [(M+H)+]. Anal. (C13H11N3OBrF3): C, H, N, Br, F.
5.1.44. 2-(4-Bromophenyl)-6-methyl-N-[2-(pyridin-3-
yl)ethyl]pyrimidin-4-amine oxalate (9s)
Pale brown crystal (yield 62%); 1H NMR (DMSO-d6) d 2.29 (3H, s),
2.93 (2H, t, J = 6.8 Hz), 3.50–4.00 (2H, m), 6.30 (1H, s), 7.35 (1H, dd,
J = 4.7, 7.8 Hz), 7.59 (1H, s), 7.68 (2H, d, J = 8.3 Hz), 7.74 (1H, d,
J = 7.8 Hz), 8.24 (2H, d, J = 8.3 Hz), 8.43 (1H, d, J = 4.7 Hz), 8.50
(1H, s); FAB-MS m/z 369, 371 [(M+H)+]. Anal. (C18H17N4
Brꢁ2C2H2O4ꢁ0.25H2O): C, H, N, Br.
5.1.36. 2-{[2-(4-Bromophenyl)-6-propylpyrimidin-4-
yl]amino}ethanol oxalate (9k)
White solid (yield 62%); 1H NMR (DMSO-d6) d 0.93 (3H, t,
J = 7.4 Hz), 1.60–1.80 (2H, m), 3.20–3.80 (4H, m), 6.32 (1H, s),
7.30–7.60 (1H, br), 7.67 (2H, d, J = 8.3 Hz), 8.24 (2H, d, J = 8.3 Hz);
FAB-MS m/z 336, 338 [(M+H)+]. Anal. (C15H18N3OBrꢁC2H2O4): C,
H, N, Br.
5.1.45. 2-(4-Bromophenyl)-6-methyl-N-[2-(1-oxidopyridin-3-
yl)ethyl]pyrimidin-4-amine oxalate (9t)
To a solution of 2-(4-bromophenyl)-6-methyl-N-[2-(pyridin-3-
yl)ethyl]pyrimidin-4-amine (9s, 1.40 g) in chloroform (20 mL)
was added m-CPBA (1.40 g), and the mixture was stirred at room
temperature for 23 h. To the reaction mixture was added addi-
tional m-CPBA (0.20 g) and the mixture was stirred at room tem-
perature for 13 h. To the reaction mixture was added saturated
aqueous sodium hydrogen carbonate (40 mL), and extracted with
chloroform. The organic layer was dried, and the desiccant was re-
5.1.37. 2-{[2-(4-Bromophenyl)-6-isopropylpyrimidin-4-
yl]amino}ethanol oxalate (9l)
White solid (yield 36%); 1H NMR (DMSO-d6) d 1.22 (6H, d,
J = 6.8 Hz), 2.70–2.90 (1H, m), 3.00–3.90 (4H, m), 6.32 (1H, s),
7.30–7.60 (1H, br), 7.67 (2H, d, J = 8.3 Hz), 7.97 (1H, s), 8.26 (2H,
d, J = 8.3 Hz); FAB-MS m/z 336, 338 [(M+H)+]. Anal. (C15H18N3OBrꢁ-
C2H2O4ꢁ0.25H2O): C, H, N, Br.