HETEROCYCLES, Vol. 85, No. 11, 2012
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(CDCl3, 500 MHz): δH 1.00, 1.02 (6H, 2d, J=1.64 Hz, 2CH3), 1.90-1.95 (1H, m, CH), 2.36, 2.39 (6H, 2s,
2CH3), 3.34-3.37 (2H, m, CH2), 5.12 (1H, br s, NH), 6.34 (1H, s, C-H of pyridine) ppm. 13C NMR
(CDCl3, 125 MHz): δC 20.59, 25.39 (2CH3 of pyridine), 20.62 (2CH3 of i-butyl), 28.84 (CH2), 49.15 (CH-
N), 89.10 (C≡N), 113.43 (C-H of pyridine), 117.42, 152.60, 159.40, 162.13 (pyridine carbons) ppm; MS:
m/z: 203 (M+), 188 (M+-CH3), 160 (M+-C3H7), 131 (M+-C4H10N), 105 (M+-C5H10N2), 57, 43; Anal. Calcd
for C12H17N3: C, 70.90; H, 8.43; N, 20.67. Found: C, 70.93; H, 8.47; N, 20.71.
2-(2-Hydroxyethylamino)-4,6-dimethylpyridine-3-carbonitrile (2g):
Colorless crystals; mp 75 °C; νmax (KBr) 3356 (N-H), 3465-3265 (O-H), 2209 (C≡N), 1568, 1536 (C-N),
1
1243 (C-O) cm-1; H NMR (CDCl3, 500 MHz): δH 2.41-2.45 (6H, 2s, 2CH3), 3.68-3.71 (2H, d of t,
J=9.38 Hz, J=5.42 Hz, CH2-NH), 3.84-3.86 (2H, t, J=4.69 Hz, CH2-OH), 4.75 (1H, br s, OH), 5.58 (1H,
br s, NH), 6.44 (1H, s, C-H of pyridine) ppm. 13C NMR (CDCl3, 125 MHz): δC 20.74, 24.92 (2CH3),
45.84 (CH2-NH), 64.62 (CH2-OH), 90.18 (C≡N), 114.40 (C-H of pyridine), 116.82, 153.70, 159.58,
161.49 (pyridine carbons) ppm; MS: m/z: 190 (M+-1), 173 (M+-H2O), 141 (M+-H2O, C2H4N+), 131 (M+-
C2H6NO), 103 (M+-C3H6N2O), 91 (C6H5N+); Anal. Calcd for C10H13N3O: C, 62.81; H, 6.85; N, 21.97.
Found: C, 62.84; H, 6.89; N, 22.04.
2-(Benzylamino)-4,6-dimethylpyridine-3-carbonitrile (2h):
1
Colorless crystals; mp 138 °C; νmax (KBr) 3392 (N-H), 2198 (C≡N), 1574, 1522 (C-N) cm-1; H NMR
(CDCl3, 500 MHz): δH 2.40, 2.43 (6H, 2s, 2CH3), 4.75 (2H, d, J=5.56 Hz, CH2), 5.42 (1H, br s, NH), 6.42
(1H, s, C-H of pyridine), 7.29-7.33, 7.37-7.41 (5H, 2m, phenyl protons) ppm. 13C NMR (CDCl3, 125
MHz): δC 20.65, 25.39 (2CH3), 45.71(CH2), 89.48 (C≡N), 114.08 (C-H of pyridine), 127.82, 128.30,
129.05, 139.42 (phenyl carbons), 117.23, 152.84, 158.90, 162.22 (pyridine carbons) ppm; MS: m/z: 237
(M+), 222 (M+-CH3), 146 (M+-C7H7), 131 (M+-PhCH2N), 107 (PhCH2N+), 91, 77; Anal. Calcd for
C15H15N3: C, 75.92; H, 6.37; N, 17.71. Found: C, 75.90; H, 6.40; N, 17.74.
4,6-Dimethyl-2-(phenethylamino)pyridine-3-carbonitrile (2i):
1
Colorless crystals; mp 106 °C; νmax (KBr) 3368 (N-H), 2208 (C≡N), 1566, 1518 (C-N) cm-1; H NMR
(CDCl3, 500 MHz): δH 2.38, 2.42 (6H, 2s, 2CH3), 2.94-2.97 (2H, t, J=7.13 Hz, CH2), 3.77-3.81 (2H, d of
t, J=13.59 Hz, J=5.97 Hz, CH2-N), 5.15 (1H, br s, NH), 6.38 (1H, s, C-H of pyridine), 7.26-7.30, 7.35-
13
7.38 (5H, 2m, phenyl protons) ppm. C NMR (CDCl3, 125 MHz): δC 20.63, 25.42 (2CH3 of pyridine),
36.28 (Ph-CH2), 43.18 (CH2-NH), 89.48 (C≡N), 113.74 (C-H of pyridine), 126.90, 129.05, 129.24,
139.58 (phenyl carbons), 117.18, 152.70, 159.02, 162.17 (pyridine carbons) ppm; MS: m/z: 251 (M+), 160
(M+-PhCH2), 131 (M+-C8H10N), 120 (C8H10N+), 91 (C6H5N+), 57, 43; Anal. Calcd for C16H17N3: C,
76.46; H, 6.82; N, 16.72. Found: C, 76.49; H, 6.84; N, 16.77.
2-(Dimethylamino)-4,6-dimethylpyridine-3-carbonitrile (2j):
1
Colorless crystals; mp 48 °C; νmax (KBr) 2198 (C≡N), 1581, 1557, 1513 (C-N) cm-1; H NMR (CDCl3,