BENTYA et al.
1070
1
1010, 940, 830, 780, 720. H NMR spectrum, δ, ppm:
3.93 t (2H, CH2, J = 4.8 Hz), 5.12 d (1H, =CH, J =
10.2 Hz), 5.21 d (1H, =CH, J = 17.1 Hz), 5.86–5.99 m
(1H, =CH), 6.54–6.63 m (1H, NH), 7.74 s (3-H),
10.42 s (1H, NH), 12.90 s (1H, NH). 13C NMR spec-
trum, δC, ppm: 42.42 (CH2), 99.39 (C3a), 115.38
(=CH2), 134.56 (C3, =CH), 153.37 (C7a) 155.88 (C6),
157.89 (C4). Found, %: C 50.44; H 4.86; N 36.39.
C8H9N5O. Calculated, %: C 50.26; H 4.74; N 36.63.
3460, 3280 (NH), 1690 (C=O), 1610, 1590, 1550,
1500, 1400, 1300, 1110, 1070, 980, 860, 780, 760,
720. H NMR spectrum, δ, ppm: 3.20–3.25 m (1H,
≡CH), 4.11–4.20 m (2H, CH2), 7.05–7.13 m (1H, NH),
7.33 t (1H, Harom, J = 7.5 Hz), 7.52 t (2H, Harom, J =
7.8 Hz), 8.08 s (3-H), 8.19 d (2H, Harom, J = 7.8 Hz),
10.98 s (1H, NH). Found, %: C 63.22; H 4.06;
N 26.39. C14H11N5O. Calculated, %: C 63.39; H 4.18;
N 26.40.
1
1-Phenyl-6-(prop-2-en-1-ylamino)-1H-pyrazolo-
[3,4-d]pyrimidin-4(5H)-one (IIb). Yield 2.38 g
(89%), mp 211–213°C (from ethanol). IR spectrum, ν,
cm–1: 3480, 3400, 3250, 3150 (NH), 1690 (C=O),
1620, 1590, 1550, 1500, 1400, 1290, 1110, 1060, 990,
8-Iodomethyl-1-R-7,8-dihydroimidazo[1,2-a]-
pyrazolo[4,3-e]pyrimidin-4(6H)-ones Va and Vb
and 6-allyl-8-iodomethyl-1-R-7,8-dihydroimidazo-
[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-ones VIa and
VIb (general procedure). A solution of 1.52 g
(6 mmol) of iodine in 150 ml of acetic acid was added
at room temperature to a suspension of 2 mmol of
6-allyl(diallyl)aminopyrazolo[3,4-d]pyrimidin-4(5H)-
one ІІa, IIb, IIIa, or IIIb in 10 ml of acetic acid, and
the mixture was stirred for 24 h. The solution was
evaporated to dryness, 30 ml of acetonitrile was added
to the residue (in the reactions with ІІa, IIIa) or the
salt-like precipitate was filtered off, washed with
diethyl ether, and dissolved in 30 ml of acetonitrile (in
the reactions with ІІb and IIIb). The solution was
treated under stirring with a 5% solution of sodium
sulfite until brown color disappeared, the mixture was
evaporated to 2/3 of the initial volume, and the precip-
itate was filtered off, washed with distilled water, and
dried in air.
1
960, 920, 830, 780, 750, 710. H NMR spectrum, δ,
ppm: 4.00 t (2H, CH2, J = 5.4 Hz), 5.15 d (1H, =CH,
J = 10.5 Hz), 5.27 d (1H, =CH, J = 17.1 Hz), 5.88–
6.01 m (1H, =CH), 6.82–6.94 m (1H, NH), 7.30 t (1H,
Harom, J = 7.5 Hz), 7.51 t (2H, Harom, J = 7.8 Hz), 8.04 s
(3-H), 8.13 d (2H, Harom, J = 7.8 Hz), 10.77 s (1H,
NH). 13C NMR spectrum, δC, ppm: 42.87 (CH2),
101.17 (C3a), 115.81 (=CH2), 120.19 (2C, Carom),
126.08 (Carom), 128.73 (2C, Carom), 134.42 (=CH),
135.83 (C3), 139.00 (Carom), 153.73 (C7a), 154.24 (C6),
157.58 (C4). Found, %: C 62.84; H 4.87; N 26.18.
C14H13N5O. Calculated, %: C 62.91; H 4.90; N 26.20.
6-Bis(prop-2-en-1-yl)amino-1H-pyrazolo[3,4-d]-
pyrimidin-4(5H)-one (IIIa). Yield 1.80 g (78%),
mp 242–244°C. IR spectrum, ν, cm–1: 3190, 3120
(NH), 1690 (C=O), 1600, 1410, 1320, 1290, 1260,
1070, 1010, 930, 770, 720. 1H NMR spectrum, δ, ppm:
4.09–4.23 m (4H, CH2), 5.11–5.24 m (4H, CH2), 5.76–
5.93 m (2H, CH), 7.80 s (3-H), 10.54 br.s (1H, NH),
12.94 br.s (1H, NH). Found, %: C 57.02; H 5.61;
N 30.17. C11H13N5O. Calculated, %: C 57.13; H 5.67;
N 30.28.
8-Iodomethyl-7,8-dihydro-1H-imidazo[1,2-a]-
pyrazolo[4,3-e]pyrimidin-4(6H)-one (Va). Yield
0.52 g (82%), mp 327–329°C. IR spectrum, ν, cm–1:
3290 (NH), 1600 (C=O), 1500, 1460, 1340, 1270,
1180, 1120, 1020, 980, 850, 780. 1H NMR spectrum, δ,
ppm: 3.32–3.38 m (1H, CH), 3.71–3.74 m (1H, CH),
3.85–3.91 m (1H, CH), 3.95–4.00 m (1H, CH), 4.60–
4.70 m (1H, CH), 8.19 s (3-H), 9.46–11.94 br.s (1H,
NH). 13C NMR spectrum, δC, ppm: 10.04 (CH2I),
47.23 (C7), 55.40 (C8), 102.34 (C3a), 128.21 (C3),
148.29 (C9a), 158.03 (C5a), 165.85 (C4). Found, %:
C 30.21; H 2.46; I 39.96; N 22.03. C8H8IN5O. Cal-
culated, %: C 30.30; H 2.54; I 40.02; N 22.09.
6-Bis(prop-2-en-1-yl)amino-1-phenyl-1H-pyra-
zolo[3,4-d]pyrimidin-4(5H)-one (IIIb). Yield 2.70 g
(88%), mp 190–192°C (from ethanol). IR spectrum, ν,
cm–1: 1710 (C=O), 1580, 1500, 1390, 1310, 1260,
1
1120, 960, 910. H NMR spectrum, δ, ppm: 4.18–
4.26 m (4H, CH2), 5.18–5.26 m (4H, CH2), 5.82–
5.97 m (2H, CH), 7.31 t (1H, Harom, J = 7.2 Hz), 7.52 t
8-Iodomethyl-1-phenyl-7,8-dihydro-1H-imidazo-
[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one (Vb).
Yield 0.61 g (78%), mp 220–222°C. IR spectrum, ν,
cm–1: 1640 (C=O), 1580, 1420, 1330, 1280, 1230,
(2H, Harom, J = 7.5 Hz), 8.07 s (3-H), 8.13 d (2H, Harom
,
J = 8.1 Hz), 10.90 s (1H, NH). Found, %: C 66.33;
H 5.46; N 22.64. C17H17N5O. Calculated, %: C 66.43;
H 5.58; N 22.79.
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1170, 1050, 1030, 990, 960, 930, 780, 760. H NMR
1-Phenyl-6-(prop-2-yn-1ylamino)-1H-pyrazolo-
[3,4-d]pyrimidin-4(5H)-one (IV). Yield 2.23 g (84%),
mp 242–244°C (from ethanol). IR spectrum, ν, cm–1:
spectrum, δ, ppm: 2.58–2.64 m (1H, CH), 2.77–2.81 m
(1H, CH), 3.25–3.29 m (1H, CH), 3.79–3.86 m (1H,
CH), 4.45–4.54 m (1H, CH), 7.59–7.77 m (5H, Harom),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 7 2011