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Suzuki Coupling in Densely Functionalized Pyrimidones
1349
7g
Anal. Calcd for C18H20N2O4: C, 65.84; H, 6.14; N, 8.53. Found: C,
65.70; H, 6.12; N, 8.40.
White solid; yield: 81%.
1H NMR (300 MHz, CDCl3): d = 8.00–7.91 (m, 5 H), 4.42 (q, J =
7.2 Hz, 2 H), 4.40 (q, J = 7.2 Hz, 2 H), 3.24 (s, 3 H), 1.46 (t, J = 7.2
Hz, 3 H), 1.38 (t, J = 7.2 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 164.3, 160.0, 154.4, 142.7, 141.6,
133.3, 131.5, 130.5, 130.1, 128.7, 127.6, 126.7, 126.5, 125.2, 124.0,
68.9, 61.9, 33.7, 15.5, 14.0.
8a
White solid; yield: 82%.
1H NMR (300 MHz, CDCl3): d = 7.48–7.21 (m, 8 H), 6.90–6.88 (m,
2 H), 5.19 (m, 2 H), 4.40 (q, J = 6.9 Hz, 2 H), 4.36 (q, J = 6.9 Hz, 2
H), 1.41 (t, J = 6.9 Hz, 3 H), 1.39 (t, J = 6.9 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 164.7, 160.3, 155.7, 143.1, 141.7,
135.8, 134.4, 130.4, 128.83, 128.76, 128.5, 128.0, 127.3, 69.2, 62.2,
49.7, 15.7, 14.4.
MS (ES+): m/z = 353 (M + H).
Anal. Calcd for C20H20N2O4: C, 68.17; H, 5.72; N, 7.95. Found: C,
67.93; H, 5.67; N, 7.90.
MS (ES+): m/z = 379 (M + H).
7j
Anal. Calcd for C22H22N2O4: C, 69.83; H, 5.86; N, 7.40. Found: C,
69.86; H, 5.87; N, 7.35.
White crystalline solid; yield: 82%.
1H NMR (300 MHz, CDCl3): d = 8.05 (s, 1 H), 7.96–7.88 (m, 3 H),
7.62–7.53 (m, 3 H), 4.42 (q, J = 7.2 Hz, 2 H), 4.37 (q, J = 7.2 Hz, 2
H), 3.51 (s, 3 H), 1.43 (t, J = 7.2 Hz, 3 H), 1.40 (t, J = 7.2 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 164.2, 159.3, 155.5, 141.4, 140.8,
133.2, 132.1, 131.6, 128.5, 128.4, 128.0, 127.7, 127.6, 127.0, 125.3,
68.0, 61.4, 34.6, 15.2, 14.0.
8b
Yellow oil; yield: 74%.
1H NMR (400 MHz, CDCl3): d = 7.36 (t, J = 1.2 Hz, 1 H), 7.22–7.14
(m, 5 H), 7.08 (d, J = 3.6 Hz, 1 H), 6.81 (d, J = 6.8 Hz, 1 H), 5.12
(d, J = 14.4 Hz, 1 H), 5.02 (d, J = 14.4 Hz, 1 H), 4.39 (q, J = 7.2 Hz,
4 H), 1.90 (s, 3 H), 1.43 (t, J = 7.2 Hz, 3 H), 1.38 (t, J = 7.2 Hz, 3 H).
13C NMR (100 MHz, CDCl3): d = 164.6, 160.4, 155.3, 143.1, 141.7,
136.5, 135.4, 133.9, 130.8, 130.3, 128.6, 128.3, 128.14, 128.06,
126.1, 69.3, 62.2, 49.0, 19.2, 15.7, 14.3.
MS (ES+): m/z = 353 (M + H).
Anal. Calcd for C20H20N2O4: C, 68.17; H, 5.72; N, 7.95. Found: C,
67.87; H, 5.62; N, 7.80.
MS (ES+): m/z = 393 (M + H).
7k
White solid yield: 84%.
Anal. Calcd for C23H24N2O4·1/2H2O: C, 68.81; H, 6.28; N, 6.98.
Found: C, 68.33; H, 6.03; N, 6.88.
1H NMR (400 MHz, CDCl3): d = 7.46 (td, J = 8.4, 1.6 Hz, 1 H), 7.39
(dd, J = 7.6, 1.6 Hz, 1 H), 7.07 (t, J = 7.6 Hz, 1 H), 7.96 (d, J = 8.4
Hz, 1 H), 4.45–4.31 (m, 4 H), 3.82 (s, 3 H), 3.35 (s, 3 H), 1.44–1.36
(m, 6 H).
13C NMR (100 MHz, CDCl3): d = 164.8, 160.3, 156.5, 153.9, 142.7,
141.9, 132.1, 130.3, 123.9, 121.4, 111.0, 69.0, 62.0, 55.7, 33.3,
15.7, 14.3.
8c
Light-yellow solid, yield: 78%.
1H NMR (300 MHz, CDCl3): d = 7.43 (m, 1 H), 7.42–7.27 (m, 4 H),
7.12 (d, J = 5.1 Hz, 1 H), 6.99–6.98 (m, 2 H), 5.27 (s, 2 H), 4.42 (q,
J = 7.2 Hz, 2 H), 4.35 (q, J = 7.2 Hz, 2 H), 1.40 (t, J = 7.2 Hz, 6 H).
13C NMR (75 MHz, CDCl3): d = 164.7, 160.2, 151.6, 143.0, 141.8,
141.6, 135.9, 134.7, 129.1, 128.3, 128.0, 127.8, 126.7, 69.3, 62.2,
49.8, 15.7, 14.4.
MS (ES+): m/z = 333 (M + H).
Anal. Calcd for C17H20N2O5·1/2H2O: C, 59.81; H, 6.20; N, 8.21.
Found: C, 59.48; H, 6.01; N, 8.29.
MS (ES+): m/z = 385 (M + H).
7l
Anal. Calcd for C20H20N2O4S: C, 62.48; H, 5.24; N, 7.29. Found: C,
61.98; H, 5.31; N, 7.09.
White solid; yield: 65%.
1H NMR (300 MHz, CDCl3): d = 10.09 (s, 1 H), 8.02 (d, J = 8.1 Hz,
2 H), 7.71 (d, 2 H, J = 8.1 Hz), 4.41 (q, J = 6.9 Hz, 2 H), 4.37 (q,
J = 6.9 Hz, 2 H), 3.46 (s, 3 H), 1.43 (t, J = 6.9 Hz, 3 H), 1.38 (t, J =
6.9 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 191.4, 164.5, 160.3, 153.8, 143.2,
141.4, 139.6, 137.6, 130.2, 129.4, 69.3, 62.3, 35.0, 15.7, 14.4.
Method C: This procedure is the same as Method B, except that 1%
of catalyst loading was used.
Compound 7b (see above for characterization) was obtained in 88%
isolated yield using this procedure.
Method D: This procedure is the same as Method A (Table 2), how-
ever, with a prolonged reaction time of 20 min. The following com-
pounds were obtained by this method:
MS (ES+): m/z = 331 (M + H).
Anal. Calcd for C17H18N2O5: C, 61.81; H, 5.49; N, 8.48. Found: C,
61.65; H, 5.44; N, 8.32.
9a
Yellow solid; yield: 84%.
7m
1H NMR (300 MHz, CDCl3): d = 7.35–7.08 (m, 10 H), 4.44 (q, J =
7.2 Hz, 2 H), 4.38 (q, J = 7.2 Hz, 2 H), 1.42 (t, J = 7.2 Hz, 3 H), 1.41
(t, J = 7.2 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 164.7, 160.0, 154.5, 143.1, 141.8,
136.9, 134.4, 129.8, 129.4, 129.3, 129.1, 128.7, 128.1, 69.2, 62.2,
15.7, 14.3.
Yellow solid; yield: 70%.
1H NMR (300 MHz, CDCl3): d = 7.93 (d, J = 15.3 Hz, 1 H), 7.71 (d,
J = 8.1 Hz, 2 H), 7.57 (m, 2 H), 7.40 (m, 3 H), 6.96 (d, J = 15.3 Hz,
2 H), 4.44 (q, J = 7.2 Hz, 2 H), 4.29 (q, J = 7.2 Hz, 2 H), 3.68 (s, 3
H), 1.44 (t, J = 7.2 Hz, 3 H), 1.38 (t, J = 7.2 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 165.0, 160.1, 151.9, 142.5, 142.2,
142.0, 135.3, 130.2, 129.1, 128.1, 117.7, 69.1, 62.1, 31.2, 15.6,
14.4.
MS (ES+): m/z = 365 (M + H).
Anal. Calcd for C21H20N2O4: C, 69.22; H, 5.53; N, 7.69. Found: C,
69.27; H, 5.53; N, 7.76.
MS (ES+): m/z = 329 (M + H).
Synthesis 2006, No. 8, 1343–1350 © Thieme Stuttgart · New York