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5.6 Hz, 8.4 Hz, 2H). 13C NMR (100 MHz, CDCl3): d ¼ 28.6, 29.9, d ¼ 3.28 (s, 3H), 3.68 (s, 3H), 5.80 (d, J ¼ 2.8 Hz, 1H), 6.81
103.6, 115.7 (d, J ¼ 21.0 Hz), 127.7, 129.1, 130.0, 131.7 (d, J ¼ (br s, 1H, NH), 7.30–7.37 (m, 3H), 7.46–7.53 (m, 4H), 7.61 (t, J
10.0 Hz), 132.4, 138.3, 151.3, 157.9, 159.6, 164.4, 165.6 (d, J ¼ ¼ 7.6 Hz, 1H), 7.89 (t, J ¼ 1.2 Hz, 2H). 13C NMR (100 MHz,
161.0 Hz), 170.5. HRMS (ESI): m/z calcd for C20H15FN4O2Na [M+ CDCl3): d ¼ 27.8, 29.4, 53.4, 89.8, 126.7, 127.2, 128.5, 128.96,
+ Na]: 385.1071; found: 385.1063.
129.0, 132.6, 133.0, 144.2, 150.6, 152.3, 159.4, 161.4.
7-(4-Chlorophenyl)-1,3-dimethyl-5-phenylpyrimido[4,5-d]
pyrimidine-2,4(1H,3H)-dione (3r)25
Conflicts of interest
The author declares no conicts of nancial interest.
White solid; Rf ¼ 0.4 (SiO2, hexane/ethyl acetate ¼ 10 : 90); yield:
80% (151 mg, 0.40 mmol), mp 259–260 ꢀC. 1H NMR (400 MHz,
CDCl3): d ¼ 3.41 (s, 3H), 3.85 (s, 3H), 7.46–7.54 (m, 5H), 7.62 (t, J
¼ 1.6 Hz, 2H), 8.52 (d, J ¼ 8.8 Hz, 2H). 13C NMR (100 MHz,
CDCl3): d ¼ 28.6, 29.9, 103.8, 127.8, 128.9, 129.1, 130.1, 130.6,
134.6, 138.3, 138.7, 151.3, 157.9, 159.5, 164.3, 170.5. HRMS
(ESI): m/z calcd for C20H15ClN4O2Na [M+ + Na]: 401.0776; found:
401.0766.
Acknowledgements
The author P. Debnath is thankful to DST (New Delhi) for
nancial assistance (Grant no. YSS/2015/001554).
Notes and references
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¨
1 (a) T. C. Kuhler, J. Fryklund, N.-A. Bergman, J. Weilitz, A. Lee
7-(4-Bromophenyl)-1,3-dimethyl-5-phenylpyrimido[4,5-d]
pyrimidine-2,4(1H,3H)-dione (3s)25
and H. Larsson, J. Med. Chem., 1995, 38, 4906; (b) P. Madsen,
L. B. Knudsen, F. C. Wiberg and R. D. Carr, J. Med. Chem.,
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Off-white solid; Rf ¼ 0.45 (SiO2, hexane/ethyl acetate ¼ 10 : 90);
yield: 80% (169 mg, 0.40 mmol), mp 255–256 ꢀC. 1H NMR (400
MHz, CDCl3): d ¼ 3.41 (s, 3H), 3.85 (s, 3H), 7.48–7.54 (m, 3H),
7.61–7.64 (m, 4H), 8.44 (dd, J ¼ 1.6 Hz, J ¼ 6.8 Hz, 2H). 13C NMR
(100 MHz, CDCl3): d ¼ 28.7, 30.0, 103.9, 127.4, 127.8, 129.1,
130.1, 130.8, 131.9, 135.1, 138.2, 151.3, 157.9, 159.5, 164.4,
170.6. HRMS (ESI): m/z calcd for C20H16BrN4O2 [M+ + H]:
423.0451; found: 423.0441.
¨
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1-Benzyl-3-methyl-5,7-diphenylpyrimido[4,5-d]pyrimidine-
2,4(1H,3H)-dione (3t)25
White solid; Rf ¼ 0.4 (SiO2, hexane/ethyl acetate ¼ 5 : 95); yield:
88% (185 mg, 0.44 mmol), mp 211–212 ꢀC. 1H NMR (400 MHz,
CDCl3): d ¼ 3.41 (s, 3H), 5.71 (s, 2H), 7.28–7.36 (m, 3H), 7.48–
7.57 (m, 6H), 7.60–7.65 (m, 4H), 8.58 (t, J ¼ 6.8 Hz, 2H). 13C NMR
(100 MHz, CDCl3): d ¼ 28.7, 45.9, 103.7, 127.7, 128.0, 128.70,
128.74, 128.8, 129.1, 129.4, 130.0, 132.4, 136.2, 136.6, 138.4,
151.2, 157.6, 159.5, 165.3, 170.7. HRMS (ESI): m/z calcd for
C
26H20N4O2Na [M+ + Na]: 443.1478; found: 443.1471.
1,3-Dibenzyl-5,7-diphenylpyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione
(3u)25
White solid; Rf ¼ 0.5 (SiO2, hexane/ethyl acetate ¼ 5 : 95);
yield: 92% (228 mg, 0.46 mmol), mp 215 ꢀC. 1H NMR (400
MHz, CDCl3): d ¼ 4.70 (s, 2H), 5.21 (s, 2H), 7.26–7.38 (m,
6H), 7.46–7.60 (m, 10H), 7.65 (t, J ¼ 1.6 Hz, 2H), 8.56 (t, J ¼
2.0 Hz, 2H). 13C NMR (100 MHz, CDCl3): d ¼ 45.0, 46.0,
103.9, 127.8, 127.9, 128.5, 128.68, 128.7, 129.1, 129.4, 130.2,
132.3, 136.2, 136.5, 136.6, 138.3, 151.1, 157.7, 159.4, 165.2,
170.7. HRMS (ESI): m/z calcd for C32H24N4O2Na [M+ + Na]:
519.1791; found: 519.1782.
1,3-Dimethyl-5,7-diphenyl-5,6-dihydropyrimido[4,5-d]
pyrimidine-2,4(1H,3H)-dione (3a0)
Yellow solid; Rf ¼ 0.4 (SiO2, hexane/ethyl acetate ¼ 50 : 50);
1
yield: 42% (73 mg, 0.21 mmol), H NMR (400 MHz, CDCl3):
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