IZMEST’EV et al.
1400
6.53 s (1H, N1H). 13C NMR spectrum (CDCl3), δC,
ppm: 21.63 (C17), 25.97 (C18), 31.80 (C12), 32.69 (C16),
31.75 (C9), 37.87 (C14), 40.25 (C15), 44.03 (C13), 63.04
(C4), 73.28 (C7), 75.13 (C5), 86.02 (C6), 129.22
(C11), 140.10 (C10), 156.09 (C2), 200.62 (C8). Mass
spectrum, m/z (Irel, %): 395.21 (100) [M + 1]+, 397.25
(98) [M + 3]+.
δC, ppm: 24.54 (C16), 25.87 (C15), 31.40 (C9), 47.09
(C7), 55.41 (C17), 56.65 (C10), 72.85 (C4), 79.49 (C5),
81.96 (C6), 82.14 (C11), 84.70 (C12), 107.53 (C13),
113.91 (C14), 156.08 (C2), 197.44 (C8). Found, %:
C 43.65; H 5.35; N 6.71. C15H22Cl2N2O7. Calculated,
%: C 43.60; H 5.37; N 6.78.
5-Acetyl-5-chloro-4-(chloromethyl)-4-hydroxy-6-
phenylhexahydropyrimidin-2-one (6c). Yield 88%
(b, from 1c), yellowish powder which decomposes on
5-Acetyl-5-chloro-4-(dichloromethyl)-4-hydroxy-
6-[(3aS,4S,6S,6aS)-6-methoxy-2,2-dimethyltetrahy-
drofuro[3,4-d][1,3]dioxol-4-yl]hexahydropyrimidin-
2-one (5b). Yield 60% (b, from 1b, 16 h), colorless
oily material. IR spectrum, ν, cm–1: 3356 (NH), 2941,
1718 (C=O), 1668 (C=O), 1440, 1388, 1218 (C–N).
1H NMR spectrum (CDCl3), δ, ppm: 1.10 s (3H,
16-H), 1.37 s (1H, 15-H), 2.48 s (3H, 9-H), 3.09 s (1H,
17-H), 4.03–4.13 m (1H, 10-H), 4.36 d (1H, 12-H, J =
5.2 Hz), 4.53–4.68 m (2H, 4-H, 11-H), 4.71 s (1H,
13-H), 5.80 s (1H, N3H), 5.95 s (1H, 7-H), 6.21 (1H,
OH), 6.69 s (1H, N1H). 13C NMR spectrum (CDCl3),
δC, ppm: 24.05 (C16), 25.76 (C15), 31.83 (C9), 55.02
(C17), 57.01 (C10), 72.89 (C4), 73.52 (C7), 78.87 (C5),
81.90 (C11), 84.34 (C12), 85.62 (C6), 107.32 (C13),
112.96 (C14), 154.66 (C2), 196.99 (C8). Found, %:
C 40.17; H 4.79; N 6.29. C15H21Cl3N2O7. Calculated,
%: C 40.24; H 4.73; N 6.26.
1
heating. H NMR spectrum (CDCl3), δ, ppm: 1.68 s
(3H, 9-H), 3.41 d and 3.75 d (1H each, 7-H, J =
11.3 Hz), 4.97 s (1H, 4-H), 6.27 s (1H, N3H), 6.42 s
(1H, OH), 6.61 s (1H, N1H). 13C NMR spectrum
(CDCl3), δC, ppm: 32.72 (C9), 47.50 (C7), 60.99 (C4),
77.52 (C5), 82.56 (C6), 128.18, 128.95, 129.13 (Ph),
133.97 (C10), 155.11 (C2), 201.69 (C8). Found, %:
C 49.18; H 4.37; N 8.80. C13H14Cl2N2O3. Calculated,
%: C 49.23; H 4.45; N 8.83.
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 16-33-00771 mol_a) and by the Ural Branch of the
Russian Academy of Sciences (project no. 18-3-3-17)
using the equipment of the Chemistry Joint Center
(Institute of Chemistry, Komi Scientific Center, Ural
Branch, Russian Academy of Sciences).
5-Acetyl-5-chloro-4-(dichloromethyl)-4-hydroxy-
6-phenylhexahydropyrimidin-2-one (5c). Yield 86%
(b, from 1c, 16 h), unstable colorless oily material. IR
spectrum, ν, cm–1: 3366 (NH), 2933, 1715 (C=O),
1670 (C=O), 1445, 1370, 1224 (C–N), 1112, 970.
1H NMR spectrum (DMSO-d6), δ, ppm: 2.24 s (3H,
9-H), 4.63 s (1H, 4-H), 5.87 s (1H, N3H), 5.98 s (1H,
7-H), 6.22 (1H, OH), 6.60 s (1H, N1H). 13C NMR
spectrum (DMSO-d6), δC, ppm: 33.22 (C9), 62.38 (C4),
74.48 (C7), 57.90 (C7), 86.43 (C6), 128.29, 129.29,
129.89 (CHPh), 134.48 (C10), 154.98 (C2), 200.02 (C8).
Found, %: C 44.35; H 3.68; N 8.03. C13H13Cl3N2O3.
Calculated, %: C 44.41; H 3.73; N 7.97.
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drofuro[3,4-d][1,3]dioxol-4-yl]hexahydropyrimidin-
2-one (6b). Yield 85% (b, from 1b), yellowish oily
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1
1103, 870. H NMR spectrum (CDCl3), δ, ppm: 1.35 s
(3H, 16-H), 1.66 s (3H, 15-H), 2.61 s (3H, 9-H), 3.27 s
(3H, 17-H), 3.60 d and 3.92 d (1H each, 7-H, J =
11.6 Hz), 4.32 d (1H, 4-H, J = 2.5 Hz), 4.59 d (1H,
12-H, J = 5.8 Hz), 4.74 d.d (1H, 11-H, J = 5.5, 3.3 Hz),
4.82 s (1H, 10-H), 4.91 s (1H, 13-H), 6.43 s (2H, N3H,
OH), 7.99 s (1H, N1H). 13C NMR spectrum (CDCl3),
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 9 2018