3314
Med Chem Res (2013) 22:3309–3315
4-(40-Benzyloxyphenyl-20-hydroxy)-6-(300,400-dimethoxyphenyl)-
2-aminopyrimidine (8k) Yield 32 %; Yellow crystals from
MeOH; mp 198–200 °C; IR (KBr) mmax: 3420, 3322,
(s, 3H, OCH3), 4.1 (s, 3H, OCH3) 5.1 (2H, NH2), 7.36
(s, 1H, Pyri), 6.9–7.8 (7H, ArH), 13.19 (br, 1H, OH); MS
m/z; 324.2 (M?1); Anal. Calcd for C18H17N3O3: C, 66.86;
H, 5.30; N, 13.00. Found: C, 66.80; H, 5.36; N, 12.90.
3210, 1647 cm-1 1H NMR (400 MHz, CDCl3): d 3.9
;
(s, 3H, OCH3), 4.0 (s, 3H, OCH3), 5.12 (s, 2H, OCH2Ar),
5.3 (2H, NH2), 6.9–7.9 (m, 12H, ArH), 7.36 (s, 1H, Pyri),
11.03 (br, 1H, OH); MS m/z; 430.2 (M?1); Anal. Calcd for
C25H23N3O4: C, 69.92; H, 5.40; N, 9.78. Found: C, 69.95;
H, 5.37; N, 9.77.
4-(20-Hydroxy-50-methoxyphenyl)-6-(200-chlorophenyl)-
2-aminopyrimidine (8f) Yield 52 %; Yellow crystals
from MeOH; mp 163–165 °C; IR (KBr) mmax: 3480, 3310,
3110, 1655 cm-1 1H NMR (400 MHz, CDCl3): d 3.8
;
(s, 3H, OCH3), 5.2 (2H, NH2), 7.39 (s, 1H, Pyri), 6.9–7.9
(7H, ArH), 13.09 (br, 1H, OH); MS m/z; 328.2 (M?1);
Anal. Calcd for C17H14ClN3O2: C, 62.30; H, 4.31; N,
12.82. Found: C, 62.34; H, 4.27; N, 12.79.
4-(40-Benzyloxyphenyl-20-hydroxy)-6-(400-fluorophenyl)-
2-aminopyrimidine (8l) Yield 45 %; Yellow crystals
from MeOH; mp 195–196 °C; IR (KBr) mmax: 3493, 3318,
1
3220, 1652 cm-1; H NMR (400 MHz, CDCl3): d 5.12
4-(20-Hydroxy-50-methoxyphenyl)-6-(300-chlorophenyl)-
2-aminopyrimidine (8g) Yield 70 %; Yellow crystals
from MeOH; mp 178–179 °C; IR (KBr) mmax: 3456, 3352,
(s, 2H, OCH2Ar), 6.5 (2H, NH2), 6.6–8.1 (m, 12H, ArH),
7.35 (s, 1H, Pyri), 12.01 (br, 1H, OH); MS m/z; 388.2
(M?1); Anal. Calcd for C23H18FN3O2: C, 71.31; H, 4.68;
N, 10.85. Found: C, 71.27; H, 4.70; N, 10.86.
3110, 1640 cm-1 1H NMR (400 MHz, CDCl3): d 3.8
;
(s, 3H, OCH3), 5.2 (2H, NH2), 7.37 (s, 1H, Pyri), 7.0–7.8
(7H, ArH), 13.84 (br, 1H, OH); 13C NMR (400 MHz,
CDCl3): d 56.13, 102.10, 111.48, 117.36, 119.37, 119.84,
125.27, 127.38, 130.08, 130.78, 135.01, 139.14, 152.24,
154.94, 160.79, 165.16, 166.00; MS m/z; 328.2 (M?1);
Anal. Calcd for C17H14ClN3O2: C, 62.30; H, 4.31; N,
12.82. Found: C, 62.36; H, 4.30; N, 12.85.
4-(40-Benzyloxyphenyl-20-hydroxy)-6-(200-chlorophenyl)-
2-aminopyrimidine (8m) Yield 35 %; Yellow crystals
from MeOH; mp 161–162 °C; IR (KBr) mmax: 3450, 3315,
1
3220, 1652 cm-1; H NMR (400 MHz, CDCl3): d 5.10
(s, 2H, OCH2Ar), 5.15 (2H, NH2), 7.34–7.39 (m, 5H, ArH),
6.55–7.71 (m, 7H, ArH), 7.35 (s, 1H, Pyri), 13.88 (br, 1H,
OH); MS m/z; 404.1 (M?1); Anal. Calcd for
C23H18ClN3O2: C, 68.40; H, 4.49; N, 10.40. Found: C,
68.40; H, 4.51; N, 10.40.
4-(20-Hydroxy-50-methoxyphenyl)-6-(400-fluorophenyl)-
2-aminopyrimidine (8h) Yield 56 %; Yellow crystals
from MeOH; mp 202–203 °C; IR (KBr) mmax: 3460, 3310,
3222, 1640 cm-1 1H NMR (400 MHz, CDCl3): d 3.8
;
4-(40-Benzyloxyphenyl-20-hydroxy)-6-(400-methylphenyl)-
2-aminopyrimidine (8n) Yield 56 %; Yellow crystals
from MeOH; mp 215–216 °C; IR (KBr) mmax: 3428, 3323,
(s, 3H, OCH3), 5.1 (2H, NH2), 7.34 (s, 1H, Pyri), 6.9–7.8
(7H, ArH), 13.16 (br, 1H, OH); MS m/z; 312.2 (M?1);
Anal. Calcd for C17H14FN3O2: C, 65.59; H, 4.53; N, 13.50.
Found: C, 65.51; H, 4.57; N, 13.54.
3204, 1647 cm-1 1H NMR (400 MHz, CDCl3): d 2.4
;
(s, 3H, CH3), 5.10 (s, 2H, OCH2Ar), 6.44 (2H, NH2), 7.2–7.4
(m, 5H, ArH), 7.4–7.8 (m, 7H, ArH), 7.35 (s, 1H, Pyri); MS
m/z; 384.1 (M?1); Anal. Calcd for C24H21N3O2: C, 75.18; H,
5.52; N, 10.96. Found: C, 75.30; H, 5.50; N, 10.90.
4-(40-Benzyloxyphenyl-20-hydroxy)-6-(400-methoxyphenyl)-
2-aminopyrimidine (8i) Yield 55 %; Yellow crystals
from MeOH; mp 226–227 °C; IR (KBr) mmax: 3495, 3347,
4-(40-Benzyloxyphenyl-20-hydroxy)-6-(300-methylphenyl)-
2-aminopyrimidine (8o) Yield 29 %; Yellow crystals
from MeOH; mp 165–167 °C; IR (KBr) mmax: 3450, 3330,
3223, 1652 cm-1 1H NMR (400 MHz, CDCl3): d 3.4
;
(s, 3H, OCH3), 5.12 (s, 2H, OCH2Ar), 6.5 (2H, NH2), 6.6–8.1
(m, 12H, ArH), 7.35 (s, 1H, Pyri), 10.07 (br, 1H, OH); MS
m/z; 400.2 (M?1); Anal. Calcd for C24H21N3O3: C, 72.16; H,
5.30; N, 10.52. Found: C, 72.21; H, 5.28; N, 10.52.
3200, 1607 cm-1 1H NMR (400 MHz, CDCl3): d 2.1
;
(s, 3H, CH3), 5.11 (s, 2H, OCH2Ar), 6.2 (2H, NH2), 7.2–7.4
(m, 5H, ArH), 6.9–7.8 (m, 7H, ArH), 7.35 (s, 1H, Pyri); MS
m/z; 384.1 (M?1); Anal. Calcd for C24H21N3O2: C, 75.18;
H, 5.52; N, 10.96. Found: C, 75.28; H, 5.51; N, 10.92.
4-(40-Benzyloxyphenyl-20-hydroxy)-6-(300-methoxyphenyl)-
2-aminopyrimidine (8j) Yield 47 %; Yellow crystals
from MeOH; mp 154–155 °C; IR (KBr) mmax: 3400, 3338,
3223, 1652 cm-1 1H NMR (400 MHz, CDCl3): d 3.9
;
Antiplasmodial activity
(s, 3H, OCH3), 5.12 (s, 2H, OCH2Ar), 5.3 (2H, NH2), 6.6–8.1
(m, 12H, ArH), 7.39 (s, 1H, Pyri), 10.53 (br, 1H, OH); MS
m/z; 400.2 (M?1); Anal. Calcd for C24H21N3O3: C, 72.16; H,
5.30; N, 10.52. Found: C, 72.18; H, 5.29; N, 10.52.
The chloroquine sensitive P. falciparum MRC 20 was
obtained from the National Institute of Malaria Research
(NIMR), New Delhi, India. The culture was synchronized
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