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filtered off and recrystallized from DMF. Yield 0.35 g
(64%), mp 308–309°C. 1H NMR spectrum (DMSO-d6–
CCl4), δ, ppm: 3.95 s (3H, OCH3), 6.58 d (1Harom
J 7 Hz), 7.09 d (1Harom, J 7 Hz), 7.29 t (1Harom, J 7 Hz),
7.53 m (2Harom), 7.59 t (1Harom, J 8 Hz), 8.12 d (2Harom
,
,
J 8 Hz), 11.76 br.s (1H, NH), 11.98 s (1H, NHindole),
12.60 br.s (1H, NH). Found, %: C 64.78; H 4.25; N 16.76.
C18H14N4O3. Calculated, %: C 64.67; H 4.22; N 16.76.
N-(7-Methoxy-4-oxo-4,5-dihydro-3H-pyrimido-
[5,4-b]indol-2-yl)benzamide (XVa). Yield 0.29 g (52%),
1
mp 311–312°C. H NMR spectrum (DMSO-d6–CCl4),
δ, ppm: 3.88 s (3H, OCH3), 6.77 d (1Harom, J 7 Hz),
6.90 s (1Harom), 7.51 t (2Harom, J 7 Hz), 7.62 t (1Harom
,
J 7 Hz), 7.88 d (1Harom, J 8 Hz), 8.13 d (2Harom, J 8 Hz),
11.81 s (1H, NH), 11.86 s (1H, NHindole.), 12.52 br.s (1H,
NH). Found, %: C 64.65; H 4.30; N 16.64. C18H14N4O3.
Calculated, %: C 64.67; H 4.22; N 16.76.
2-[(4,6-Dimethylpyrimidin-2-yl)amino]-9-
methoxy-3H-pyrimido[5,4-b]indol-4(5H)-one (XVc).
To a mixture of 0.41 g (1.86 mmol) of carboxylate Ia and
0.28 g (1.86 mmol) of N-(4,6-dimethylpyrimidin-2-
yl)cyanamide (XIIIb) in dioxane was added 0.17 ml
(1.90 mmol) of concn. HCl, and the mixture was boiled
for 1 h. On cooling the reaction mixture was poured into
100 ml of dilute ammonia solution. The precipitate was
filtered off, washed with distilled water, and recrystallized
1
from DMF. Yield 0.36 g (58%), mp 335–337°C. H NMR
spectrum (DMSO-d6–CCl4), δ, ppm: 3.98 s (3H, OCH3),
6.56 d (1Harom, J 7 Hz), 6.81 s (1Harom), 7.08 d (1Harom
,
J 7 Hz), 7.37 t (1Harom, J 8 Hz), 10.41 br.s (1H, NH),
11.72 s (1H, NHindole.), 13.60 br.s (1H, NH). Found, %:
C 60.65; H 4.84; N 25.08. C17H16N6O2. Calculated, %:
C 60.71; H 4.79; N 24.99.
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Gusakova, N.V., Izv. Akad. Nauk, Ser. Khim., 2008, p. 164.
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vol. 3, p. 3540; Omura, K., Marumoto, R., and Furukawa, Y.,
Chem. Pharm. Bull., 1981, vol. 29, p. 1870; Rajasekha-
ran, K.N., Thomas, L., Indian J. Chem., 1983, vol. 22, p. 76.
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vol. 39, p. 3434; Shishoo, C.J., Devani, M.B., Pathak, U.S.,
Ananthan, S., Bhadti, V.S., Ullas, G.V., Jain, K.S., Ra-
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The study was carried out under a financial support
of InterBioScreen Company.
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