354
P. T. Mistry, N. R. Kamdar, D. D. Haveliwala, and S. K. Patel
Vol 49
3,7-Dimethyl-1,4-diphenyl-4,6-dihydropyrazolo[40,30:5,6]
pyrano[2,3-d]pyrimidine-5(1H)-one (6a). Dark brown solid;
72%; mp: 187–190ꢁC; IR (KBr) t (cmꢀ1): 3432 (ANH), 3070,
2924 (Ar CAH), 1712 (>C¼¼O), 1603 (AC¼¼N), 1159, 1098
(CAOAC); 1H NMR (400 MHz, CDCl3) d (ppm): 10.12
(s, 1H, ANH), 8.01–7.12 (m, 10H, ArAH), 4.94 (s, 1H,
ACH), 2.15 (s, 3H, ACH3) 1.73 (s, 3H, ACH3); 13C NMR
(300 MHz, CDCl3) d (ppm): 14.31 (CH3), 20.05 (CACH3 of
pyrimidone ring), 38.25 (CH), 94.39 (C), 99.46 (C), 122.33
(CH), 124.97 (CH), 126.82 (CH), 128.68 (CH), 129.27 (CH),
137.90 (C), 143.81 (C), 145.07 (CACH3 of pyrimidone ring),
162.40 (C), 165.17 (>C¼¼O); Anal. Calcd for C22H18N4O2: C
71.34, H 4.90, N 15.13; Found: C 71.36, H 4.89, N 15.15.
4-(4-Methoxyphenyl)-3,7-dimethyl-1-phenyl-4,6-dihydropyr-
azolo[40,30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one (6b). Reddish
brown solid; 69%; mp; 242–245ꢁC; IR (KBr) t (cmꢀ1): 3156
(ANH), 3074 (Ar C-H), 1731 (>C¼¼O), 1627 (AC¼¼N), 1222,
1038 (AOCH3), 1132, 1058 (CAOAC); 1H NMR (400 MHz,
CDCl3) d (ppm): 11.14 (s, 1H, ANH), 7.98–6.75 (m, 9H, Ar-
H), 4.87 (s, 1H, ACH), 3.71 (s, 3H, -OCH3), 2.45 (s, 3H,
ACH3), 1.79 (s, 3H, ACH3); 13C NMR (300 MHz, CDCl3) d
(ppm): 14.23 (CH3), 19.96 (CACH3 of pyrimidone ring),
38.32 (CH), 54.82 (CAOCH3), 94.53 (C), 100.10 (C), 112.38
(CH), 122.51 (CH), 127.17 (CH), 128.22 (CH), 129.35 (CH),
138.02 (C), 140.20 (C), 144.11 (C), 145.23 (CACH3 of pyri-
midone ring), 159.69 (CAOCH3), 162.51 (C), 165.23
(>C¼¼O); Anal. Calcd for C23H20N4O3: C 68.99, H 5.03, N
13.99; Found: C 69.01, H 5.05, N 14.00.
(CH3), 37.06 (CH), 94.52 (C), 99.43 (C), 122.50 (CH), 125.37
(CH), 126.82 (CH), 127.97 (CH), 129.33 (CH), 131.13 (CH),
135.53 (CACl), 138.34 (CH of pyrimidone ring), 143.13 (C),
144.02 (C), 145.79 (C), 162.19 (C), 165.45 (>C¼¼O); Anal.
Calcd for C21H15N4O2Cl: C 64.54, H 3.87, N 14.34; Found: C
64.56, H 3.85, N 14.33.
4-(4-Chlorophenyl)-3-methyl-1-phenyl-4,6-dihydropyrazolo
[40,30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one
(5g). Yellow
solid; 71%; mp: 252–254ꢁC; IR (KBr) t (cmꢀ1): 3153
(ANH), 3066 (Ar C-H), 1732 (>C¼¼O), 1634 (AC¼¼N),
1138, 1066 (CAOAC), 758 (CACl); 1H NMR (400 MHz,
CDCl3) d (ppm): 11.48 (s, 1H, ANH), 8.16 (s, 1H, ACH of
pyrimidone ring), 7.94–6.76 (m, 9H, Ar-H), 4.86 (s, 1H,
ACH), 1.82 (s, 3H, ACH3); 13C NMR (300 MHz, CDCl3) d
(ppm): 14.31 (CH3), 37.96 (CH), 94.43 (C), 99.68 (C),
122.66 (CH), 128.21 (CH), 129.09 (CH), 130.27 (CH),
131.10 (CACl), 138.87 (CH of pyrimidone ring), 142.94 (C),
144.13 (C), 163.13 (C), 165.30 (>C¼¼O); Anal. Calcd for
C21H15N4O2Cl: C 64.54, H 3.87, N 14.34; Found: C 64.55, H
3.90, N 14.36.
3-Methyl-4-(3-nitrophenyl)-1-phenyl-4,6-dihydropyrazolo[40,
30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one (5h). Light brown
solid; 67%; mp: >280ꢁC; IR (KBr) t (cmꢀ1): 3146 (ANH),
3057 (Ar C-H), 1722 (>C¼¼O), 1626 (AC¼¼N), 1536, 1359
(ANO2 asym, sym), 1133, 1070 (CAOAC); 1H NMR (400
MHz, CDCl3) d (ppm): 11.49 (s, 1H, ANH), 8.14 (s, 1H,
ACH of pyrimidone ring), 7.97–6.75 (m, 9H, Ar-H), 4.87 (s,
1H, ACH), 1.81 (s, 3H, ACH3); 13C NMR (300 MHz, CDCl3)
d (ppm): 14.31 (CH3), 36.19 (CH), 94.61 (C), 99.83 (C),
122.57 (CH), 124.65 (CH), 128.32 (CH), 129.27 (CH), 133.13
(CH), 138.59 (CH of pyrimidone ring), 143.41 (C), 145.09
(C), 148.89 (CANO2), 162.12 (C), 165.37 (>C¼¼O); Anal.
Calcd for C21H15N5O4: C 62.84, H 3.77, N 17.45; Found: C
62.83, H 3.79, N 17.43.
4-(4-Hydroxyphenyl)-3,7-dimethyl-1-phenyl-4,6-dihydropyr-
azolo[40,30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one (6c). Brown
solid; 58%; mp: 259–262ꢁC; IR (KBr) t (cmꢀ1): 3262 (AOH),
3151 (ANH), 3065 (Ar CAH), 1738 (>C¼¼O), 1625 (AC¼¼N),
1
1139, 1052 (CAOAC); H NMR (400 MHz, CDCl3) d (ppm):
11.12 (s, 1H, ANH), 7.94–6.72 (m, 9H, Ar-H), 5.34 (s, 1H,
AOH), 4.83 (s, 1H, ACH), 2.42 (s, 3H, ACH3), 1.81 (s, 3H,
ACH3); 13C NMR (300 MHz, CDCl3) d (ppm): 14.63 (CH3),
19.89 (CACH3) of pyrimidone ring), 38.13 (CH), 94.74 (C),
99.59 (C), 117.10 (CH), 122.35 (CH), 127.03 (CH), 128.27
(CH), 129.41 (CH), 138.15 (C), 139.85 (C), 144.82 (C),
145.04 (CACH3 of pyrimidone ring), 153.78 (CAOH), 162.62
(C), 165.57 (>C¼¼O); Anal. Calcd for C22H18N4O3: C 68.38,
H 4.70, N 14.50; Found: C 68.37, H 4.69, N 14.52.
4-(3-Bromophenyl)-3-methyl-1-phenyl-4,6-dihydropyrazolo[40,
30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one (5i). Light brown
solid; 62%; mp: >280ꢁC; IR (KBr) t (cmꢀ1): 3150 (ANH),
3065 (Ar C-H), 1732 (>C¼¼O), 1642 (AC¼¼N), 1138, 1076
1
(CAOAC), 862 (C-Br); H NMR (400 MHz, CDCl3) d (ppm):
11.44 (s, 1H, ANH), 8.12 (s, 1H, ACH of pyrimidone ring),
7.92–6.75 (m, 9H, Ar-H), 4.85 (s, 1H, ACH), 1.79 (s, 3H,
ACH3); 13C NMR (300 MHz, CDCl3) d (ppm): 14.47 (CH3),
38.35 (CH), 94.53 (C), 99.71 (C), 122.39 (CH), 124.94 (C-Br),
127.11 (CH), 128.29 (CH), 129.54 (CH), 131.19 (CH), 138.44
(CH of pyrimidone ring), 143.35 (C), 145.21 (C), 160.23 (C),
165.71 (>C¼¼O); Anal. Calcd for C21H15N4O2Br: C 57.95, H
3.47, N 12.87; Found: C 57.97, H 3.44, N 12.86.
4-(4-Fluorophenyl)-3,7-dimethyl-1-phenyl-4,6-dihydropyra-
zolo[40,30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one (6d). Brown
solid; 55%; mp: >280ꢁC; IR (KBr) t (cmꢀ1): 3146 (ANH),
3072 (Ar C-H), 1727 (>C¼¼O), 1633 (AC¼¼N), 1135, 1060
1
(CAOAC), 747 (C-F); H NMR (400 MHz, CDCl3) d (ppm):
3-Methyl-4-(4-methylphenyl)-1-phenyl-4,6-dihydropyrazolo
[40,30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one
11.15 (s, 1H, ANH), 7.90–6.69 (m, 9H, Ar-H), 4.86 (s, 1H,
ACH), 2.46 (s, 3H, ACH3), 1.80 (s, 3H, ACH3); 13C NMR
(300 MHz, CDCl3) d (ppm): 14.81 (CH3), 19.79 (CACH3 of
pyrimidone ring), 38.52 (CH), 94.66 (C), 99.80 (C), 116.91
(CH), 122.36 (CH), 128.14 (CH), 129.33 (CH), 138.30 (C),
141.80 (C), 144.92 (C), 145.13 (CACH3 of pyrimidone ring),
159.78 (C-F), 162.81 (C), 165.55 (>C¼¼O); Anal. Calcd for
C22H17N4O2F: C 68.03, H 4.41, N 14.43; Found: C 68.01, H
4.42, N 14.41.
(5j). Cream
solid; 61%; mp: 273–275ꢁC; IR (KBr) t (cmꢀ1): 3148 (ANH),
3060 (Ar C-H), 2854 (ACH3), 1740 (>C¼¼O), 1635 (AC¼¼N),
1
1131, 1071 (CAOAC); H NMR (400 MHz, CDCl3) d (ppm):
11.46 (s, 1H, ANH), 8.14 (s, 1H, ACH of pyrimidone ring),
7.89–6.72 (m, 9H, Ar-H), 4.87 (s, 1H, ACH), 2.33 (s, 3H,
ACH3), 1.81 (s, 3H, ACH3); 13C NMR (300 MHz, CDCl3) d
(ppm): 14.61 (CH3), 22.41 (CACH3 of phenyl ring), 38.29
(CH), 94.66 (C), 99.59 (C), 122.51 (CH), 127.23 (CH), 128.03
(CH), 129.44 (CH), 130.26 (CH), 134.88 (CACH3 of phenyl
ring), 138.30 (CH of pyrimidone ring), 142.85 (C), 144.12 (C),
163.10 (C), 165.52 (>C¼¼O); Anal. Calcd for C22H18N4O2: C
71.34, H 4.90, N 15.13; Found: C 71.37, H 4.88, N 15.11.
4-(2-Chlorophenyl)-3,7-dimethyl-1-phenyl-4,6-dihydropyra-
zolo[40,30:5,6]pyrano[2,3-d]pyrimidine-5(1H)-one (6e). Dark
brown solid; 52%; mp: 202–205ꢁC; IR (KBr) t (cmꢀ1): 3142
(ANH), 3070 (Ar C-H), 1733 (>C¼¼O), 1629 (AC¼¼N), 1142,
1
1058 (CAOAC), 755 (CACl); H NMR (400 MHz, CDCl3) d
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet