C. Barillari, D. Barlocco, L. F. Raveglia
FULL PAPER
1
(s, 3 H, CH3), 2.68 (t, ϭ 6.92 Hz, 2 H,
Ph), 3.21 (m, 2 H, 7f: ESIMS:
/
ϭ 345 [MHϩ]. H NMR (CDCl3): δ ϭ 1.33Ϫ1.17
NH), 4.76 (br. s, 3 H, NH2, NH), 5.20 (s, 1 H, pyrimidine H), (m, 2 H, piperidine:
CH), 1.84Ϫ1.71 (m, 5 H), 2.47 (s, 3 H,
7.17 (d, ϭ 7.8 Hz, 2 H, Ph), 7.19 (dd, ϭ 6.9, 6.9 Hz, 1 H, CH3), 2.82 (dt, ϭ 13.2, 2.8 Hz, 2 H, piperidine CH2axN), 4.03
Ph), 7.28 (dd, ϭ 7.8, 6.9 Hz, 2 H, Ph). IR (KBr): ν˜ ϭ 3457, (t, ϭ 6.3 Hz, 2 H, OCH2), 4.31 (br. d, ϭ 13.2 Hz, 2 H, piperid-
3243, 3086, 2929, 1641, 1590 cmϪ1
.
ine CH2eqN), 4.40 (br. s, 2 H, NH2), 5.31 (s, 1 H, pyrimidine H),
6.90 (d, ϭ 8.5 Hz, 2 H, Ph), 6.94 (dd, ϭ 7.2, 7.2 Hz, 1 H,
PH), 7.28 (dd, ϭ 8.5, 7.2 Hz, 2 H, Ph). IR (KBr): ν˜ ϭ 3373,
The same procedure was followed for the synthesis of all the other
pyrimidine compounds whose spectroscopic data are reported be-
low.
2923, 1577, 1492 cmϪ1
.
1
8a: ESIMS:
/
ϭ 243 [MHϩ]. H NMR (CDCl3): δ ϭ 1.77Ϫ1.55
6b: EIMS: / ϭ 258 [Mϩ.], 165, 151, 138, 124. 1H NMR (CDCl3):
δ ϭ 2.06 (m, 2 H, chain: CH2), 2.32 (s, 3 H, CH3), 3.41 (dt,
6.5, 6.3 Hz, 2 H, NH), 4.06 (t, ϭ 6.0 Hz, 2 H, OCH2), 4.39
(m, 4 H, chain CH2), 2.66 (t, ϭ 7.5 Hz, 2 H, CH2Ph), 3.19 (dt,
ϭ 6.6, 6.6 Hz, 2 H, NH), 4.58 (br. s, 2 H, NH2), 4.77 (br. s,
1 H, NH), 5.34 (s, 1 H, pyrimidine 5-H), 7.31Ϫ7.13 (m, 5 H, Ph),
ϭ
(br. s, 2 H, NH2), 4.86 (br. t, ϭ 6.3 Hz, 1 H, NH), 5.26 (s, 1 H,
pyrimidine H), 6.90 (d, ϭ 8.8 Hz, 2 H, Ph), 6.95 (dd, ϭ 7.6,
7.6 Hz, 1 H, Ph), 7.29 (dd, ϭ 8.8, 7.6 Hz, 2 H, Ph).
˜
8.08 (s, 1 H, pyrimidine 2-H). IR (KBr): ν ϭ 3456, 3234, 1594,
1477 cmϪ1
.
8b: ESIMS:
/
ϭ 245 [MHϩ], 267 [MNaϩ]. 1H NMR (CDCl3):
δ ϭ 2.09 (m, 2 H, chain CH2), 3.45 (dt, ϭ 6.6, 6.3 Hz, 2 H,
NH), 4.07 (t, ϭ 5.7 Hz, 2 H, OCH2), 4.81 (br. s, 2 H, NH2),
1
6c: ESIMS:
/
ϭ 183 [MHϩ], 205 [MNaϩ]. H NMR (DMSO):
δ ϭ 1.61 (m, 2 H, chain: CH2), 2.10 (s, 3 H, CH3), 3.14 (dt,
ϭ
7.3, 7.3 Hz, 2 H,
(s, 1 H, pyrimidine H), 5.88 (br. s, 2 H, NH2), 6.32 (br. t,
NH), 3.44 (t, ϭ 6.3 Hz, 2 H, OCH2), 5.18
5.40 (br. s, 1 H, NH), 5.40 (s, 1 H, pyrimidine 5-H), 6.91 (d,
8.5 Hz, 2 H, Ph), 6.96 (dd, ϭ 7.2, 7.2 Hz, 1 H, Ph), 7.30 (dd,
ϭ
ϭ
6.0 Hz, 1 H, NH). IR (KBr): ν˜ ϭ 3364, 3161, 2924, 2853, 1599,
1463 cmϪ1
ϭ 8.5, 7.2 Hz, 2 H, Ph), 8.07 (s, 1 H, pyrimidine 2-H). IR
Ϫ1
.
˜
(KBr): ν ϭ 3445, 1686, 1442 cm
.
1
6d: 21.8 mg (89% overall yield) of compound 6d were obtained
from 190 mg of resin (loading 0.6 mmol/g). ESIMS: ϭ 215
[MHϩ]. H NMR (DMSO): δ ϭ 2.26 (s, 3 H, CH3), 4.43 (d,
8c. ESIMS:
/
ϭ 169 [MHϩ]. H NMR (CDCl3): δ ϭ 1.7 (br. s,
/
1 H), 2.15 (m, 2 H), 3.82 (t, ϭ 5.6 Hz, 2 H), 4.48 (t, ϭ 6.0 Hz,
2 H), 4.81 (br. s, 2 H), 5.40 (br. s, 1 H), 5.42 (s, 1 H), 8.05 (s, 1 H).
IR (KBr): ν ϭ 3397, 2885, 1669 cm
8d:[22] ESIMS: ϭ 201 [MHϩ].
ϭ 187 [MHϩ].
1
ϭ
Ϫ1
5.4 Hz, 2 H, CH2), 5.36 (s, 1 H, pyrimidine H), 6.80 (br. s, 2 H,
NH2), 7.36- 7.21 (m, 5 H, Ph), 7.93 (br. s, 1 H, NH). IR (KBr):
˜
.
/
ν˜ ϭ 3157, 1592, 1451 cmϪ1
.
8e: ESIMS:
/
6e:[21] ESIMS:
/
ϭ 201 [MHϩ].
1
8f: ESIMS:
H, piperidine
2.8 Hz, 2 H, piperidine
/
ϭ 299 [MHϩ]. H NMR (CDCl3): δ ϭ 1.26 (m, 2
1
6f: ESIMS:
/
ϭ 313 [MHϩ]. HNMR (CDCl3): δ ϭ 1.86Ϫ1.69
CH), 1.88Ϫ1.70 (m, 5 H), 2.86 (dt, ϭ 12.9,
(m, 7 H), 2.36 (s, 3 H, CH3), 2.81 (dt, ϭ 13.2, 2.8 Hz, 2 H,
piperidine N), 4.03 (t, ϭ 6.3 Hz, 2 H, OCH2), 4.32 (br. d,
ϭ 13.2 Hz, 2 H, piperidine N), 4.46 (br. s, 2 H, NH2), 5.43
N), 4.03 (t, ϭ 6.3 Hz, 2 H, OCH2),
4.30 (br. d, ϭ 12.9 Hz, 2 H, piperidine CH2eqN), 4.65 (br. s, 2
H, NH2), 5.58 (s, 1 H, pyrimidine 5-H), 6.90 (d, ϭ 8.8 Hz, 2 H,
Ph), 6.94 (dd, ϭ 7.2.7.2 Hz, 1 H, Ph), 7.28 (dd, ϭ 8.8, 7.2 Hz,
(s, 1 H, pyrimidine H), 6.89 (d, ϭ 8.8 Hz, 2 H, Ph), 6.94 (dd,
ϭ 7.2 Hz, 1 H, Ph), 7.28 (dd, ϭ 8.8, 7.2 Hz, 2 H, Ph). IR
˜
2 H, Ph), 8.17 (s, 1 H, pyrimidine 2-H). IR (KBr): ν ϭ 3345,
Ϫ1
˜
(KBr): ν ϭ 3370, 2919, 1587, 1504 cm
.
3189, 2923, 1659, 1597, 1493 cmϪ1
.
1
7a: ESIMS:
/
ϭ 289 [MHϩ]. H NMR (CDCl3): δ ϭ 1.77Ϫ1.56
1
9a: ESIMS:
/
ϭ 243 [MHϩ]. H NMR (CDCl3): δ ϭ 1.77Ϫ1.56
(m, 4 H, chain CH2), 2.45 (s, 3 H, CH3), 2.65 (t, ϭ 7.2 Hz, 2 H,
Ph), 3.19 (dt, ϭ 6.9, 6.9 Hz, 2 H, NH), 4.46 (br. s, 2 H,
NH2), 4.63 (br. t, ϭ 6.9 Hz, 1 H, NH), 5.08 (s, 1 H, pyrimidine
(m, 4 H, chain CH2), 2.65 (t, ϭ 7.6 Hz, 2 H, CH2Ph), 3.38 (dt,
ϭ 6.9, 6.6 Hz, 2 H, NH), 4.56 (br. s, 2 H, NH2), 4.90 (br. s,
1 H, NH), 5.76 (d, ϭ 5.7 Hz, 1 H, pyrimidine 5-H), 7.20Ϫ7.13
(m, 3 H, Ph), 7.3Ϫ7.23 (m, 2 H, Ph), 7.87 (d, ϭ 5.7 Hz, 1
˜
H), 7.21Ϫ7.15 (m, 3 H, - Ph), 7.28 (m, 2 H, Ph). IR (KBr): ν ϭ
3404, 3285, 3148, 2929, 1631, 1591, 1492 cmϪ1
.
Ϫ1
˜
H, pyrimidine 6-H). IR (KBr): ν ϭ 3306, 2890, 1557 cm
.
1
ϭ 245 [MHϩ]. H NMR (CDCl3): δ ϭ 2.08 (m, 2
7b: 17.7 mg (90% overall yield) of compound 7b were obtained
from 113 mg of resin (loading 0.6 mmol/g). ESIMS: ϭ 291
[MHϩ]. H NMR (CDCl3): δ ϭ 2.06 (m, 2 H, chain CH2), 2.46 (s,
3 H, CH3), 3.44(dt, ϭ 6.6, 6.6 Hz, 2 H, NH), 4.06 (t,
6.3 Hz, 2 H, OCH2), 4.46 (br. s, 2 H, NH2), 4.96 (br. s, 1 H, NH),
5.14 (s, 1 H, pyrimidine H), 6.90 (d, ϭ 8.8 Hz, Ph), 6.96 (dd,
9b: ESIMS:
/
/
H, chain CH2), 3.58 (dt, ϭ 6.9, 6.6 Hz, 2 H,
6.0 Hz, 2 H, OCH2), 4.70 (br. s, 2 H, NH2), 4.76 (br. s, 1 H, NH),
5.77 (d, ϭ 6.0, 1 H, pyrimidine 5-H), 6.95Ϫ6.88 (m, 3 H, Ph),
7.27 (m, 2 H, Ph), 7.8 (d, ϭ 6.0 Hz, 1 H, pyrimidine 6-H). IR
NH), 4.06 (t,
1
ϭ
Ϫ1
˜
(KBr): ν ϭ 3334, 2887, 1651, 1359 cm
.
ϭ 7.5, 7.5 Hz, 1 H, Ph), 7.29 (dd, ϭ 8.8, 7.5 Hz, 2 H, Ph).
1
ϭ 169 [MHϩ]. H NMR (CDCl3): δ ϭ 1.87 (br. s,
Ϫ1
9c: ESIMS:
/
˜
IR (KBr): ν ϭ 3385, 2924, 1582, 1496 cm
.
1 H, OH), 2.09 (m, 2 H, chain CH2), 3.58 (m, 2 H, CH2NH), 4.45
(t, ϭ 6.0 Hz, 2 H, OCH2), 5.63 (br. s, 2 H, NH2), 5.92 (d,
6.9 Hz, 1 H, pyrimidine 5-H), 7.69 (d, ϭ 6.9 Hz, 1 H, pyrimidine
1
7c: ESIMS:
/
ϭ 215 [MHϩ]. H NMR (CDCl3): δ ϭ 1.82 (m, 2
ϭ
H, chain CH2), 2.01 (br. s, 1 H, OH), 2.49 (s, 3 H, CH3), 3.43 (br.
s, 2 H, NH), 3.74 (t, ϭ 5.7 Hz, 2 H, OCH2), 5.17 (s, 1 H,
pyrimidine H), 5.39 (br. s, 3 H, NH2, NH). IR (KBr): ν ϭ 3333,
2890, 1651, 1557 cmϪ1
˜
6-H), 9.38 (br. s, 1 H, NH). IR (KBr): ν ϭ 3395, 3054, 2986,
1651 cmϪ1
.
˜
.
1
9d: ESIMS:
/
ϭ 201 [MHϩ]. H NMR (CDCl3): δ ϭ 4.6 (br. s,
7d:[8] ESIMS: ϭ 247 [MHϩ]. H NMR (CDCl3): δ ϭ 2.46 (s, 2 H, NH2), 4.6 (d, ϭ 6.0 Hz, 2 H, CH2), 5.34 (br. s, 1 H, NH),
/
1
3 H, CH3), 4.43 (d, ϭ 6.0 Hz, 2 H, CH2), 4.64 (br. s, 3 H, NH, 5.81 (d, ϭ 5.7 Hz, 1 H, pyrimidine 5-H), 7.36Ϫ7.21 (m, 5 H, Ph),
˜
NH2), 5.12 (s, 1 H, pyrimidine H), 7.38Ϫ7.25 (m, 5 H, Ph). IR 7.89 (d, ϭ 5.7 Hz, 1 H, pyrimidine 6-H). IR (KBr): ν ϭ 3471,
Ϫ1
(KBr): ν ϭ 3380, 2924, 1578, 1495 cm
.
3328, 3190, 1641, 1589, 1430 cmϪ1
.
˜
4740
2001, 4737Ϫ4741