2096
BABUSHKINA et al.
3
3
(
CDCl ), δ, ppm: 1.42 t (6H, POСН CH , J = 6.8 Hz),
(CH СN), 158.61 (C=O), 159.02 d (N=CS, J
=
СР
3
2
3
HH
3
3
1
2
.17 s (3H, CH ), 2.40 s (3H, CH ), 4.39 d. q (4H, POСН ,
10.1 Hz). P NMR spectrum (CDCl ): δ 1.51 ppm.
3 Р
3
3
2
=
3
3
3
JHH = 6.8, J = 12.4 Hz), 7.72 d (1H, CH=CP, JHP
HP
Diisopropyl (6-ethyl-7-methyl-5-oxo-5H-
thiazolo[3,2-a]pyrimidin-3-yl)phosphonate (5f). Yield
83%, colorless crystals, mp 117°С. H NMR spectrum
CDCl ), δ, ppm: 1.11 t (3H, CH СН , J = 7.5 Hz),
.33 d [6H, POСН(CH ) , J = 6.2 Hz], 1.41 d [6H,
6
(
6
1
2
.0 Hz). 13C NMR spectrum (CDCl ), δ , ppm: 11.37
3
С
3
CH ), 16.46 d (POСН CH , J = 5.9 Hz), 21.71 (СН ),
4.02 d (POCH , J = 5.3 Hz), 113.16 (C–С=О),
25.95d(CH=CP, J =14.4Hz), 128.04d(CH=CP, J =
13.1 Hz), 158.291 (CH СN), 158.65 (C=O), 158.98 d
1
3
2
3
СР
3
2
3
2
2
СР
(
1
3
3
2
HH
1
3
СР
СР
3 2 HH
3
3
POСН(CH ) , J = 6.2 Hz], 2.37 s (3H, CH СN),
3
2
HH
3
3
31
(
N=CS, J = 10.2 Hz). P NMR spectrum (CDCl3):
3
СР
2
.52 q (2H, CH CH , J = 7.5 Hz), 5.03 d. sept (2H,
POСН, J = 6.2, J = 12.6 Hz), 7.69 d (1H, CH=CP,
JHP = 7.7 Hz). C NMR spectrum (CDCl ), δ , ppm:
2.77 (CH СН ), 19.33 (СН СN), 21.35 (CH CH ), 23.81
3 2 HH
δР 1.44 ppm.
3
3
HH
HP
Diisopropyl (6,7-dimethyl-5-oxo-5H-thiazolo[3,2-a]-
pyrimidin-3-yl)phosphonate (5c). Yield 81%, colorless
crystals, mp 123°С. H NMR spectrum (CDCl ), δ, ppm:
.27 d [6H, POСН(CH ) , J = 6.2 Hz], 1.32 d [6H,
POСН(CH ) , J = 6.2 Hz], 2.03 s (3H, CH ), 2.31 s
3H, CH ), 4.79–4.88 d. sept (2H, POСН, J = 6.2,
3
13
3
С
1
3 2 3 3 2
1
3
3
d [POСН(CH ) , J = 4.7 Hz], 24.26 d [POСН(CH ) ,
3 2 СР 3 2
3
1
3
2
3
2
HH
JСР = 4.7 Hz], 72.81 d (POCH, J = 6.3 Hz), 119.05
(C–С=О), 125.24 d (CH=CP, J = 13.7 Hz), 129.37 d
CH=CP, J = 221.6 Hz), 158.29 (CH СN), 158.50
C=O), 159.26 d (N=CS, J = 9.7 Hz). P NMR
СР
3
2
3
2
HH
3
СР
3
(
1
3
HH
(
(
СР
3
3
3
13
JHP = 12.5 Hz), 8.02 d (1H, CH=CP, J = 7.6 Hz). C
3
31
HP
СР
NMR spectrum (CDCl ), δ , ppm: 11.51 (CH ), 22.22
СН ), 23.91 d [POСН(CH ) , J = 4.7 Hz], 24.41 d
POСН(CH ) , J = 4.7 Hz], 72.34 d (POCH, J
.3 Hz), 112.03 (C–С=О), 127.80 d (CH=CP, J
4.1 Hz), 128.12 d (CH=CP, J = 220.6 Hz), 158.58
CH СN), 159.03 (C=O), 159.80 d (N=CS, J = 9.6
Hz). P NMR spectrum (CDCl ): δ –0.79 ppm.
3
С
3
spectrum (CDCl ): δ –0.82 ppm.
3
P
3
(
[
6
1
(
3 3 2 СР
2
2
Dimethyl (7-methyl-5-oxo-6-propyl-5H-thia-
zolo[3,2-a]pyrimidin-3-yl)phosphonate (5g). Yield
51%, colorless crystals, mp 73°С. H NMR spectrum
(CDCl ), δ, ppm: 0.98 t (3H, CH СН , J = 7.4 Hz),
1.52 sext (2H, CH CH CH , J = 7.4 Hz), 2.28 s
CH СN), 2.57 t (2H, CH CH CH , J = 7.4 Hz), 3.98 d
6H, POCH , J = 11.6 Hz), 7.72 d (1H, CH=CP,
JHP = 7.6 Hz). C NMR spectrum (CDCl ), δ , ppm:
=
=
3
2
СР
СР
2
СР
1
1
СР
3
3
3
3
2
HH
3
3
СР
3
1
3
2
2
HH
3
3
P
(
3
2
2
3
HH
Dimethyl (6-ethyl-7-methyl-5-oxo-5H-thia-
zolo[3,2-a]pyrimidin-3-yl)phosphonate (5d). Yield
5%, colorless crystals, mp 112°С. H NMR spectrum
3
(
3
HP
13
3
1
3
C
6
(
2
1
2
4.20 (CH СН ), 21.46 (СН СN), 21.61 (CH CH CH ),
3
3 2 3 3 2 2
CDCl ), δ, ppm: 1.05 t (3H, CH СН , J = 7.5 Hz),
3 3 2 HH
2
7.96 (CH CH CH ), 54.37 d (POCH , J = 6.2 Hz),
119.13 (C–С=О), 126.00 d (CH=CP, JСР = 13.8 Hz),
127.87 d (CH=CP, JСР = 222.2 Hz), 157.66 (CH3СN),
59.21 (C=O), 159.45 d (N=CS, J = 10.6 Hz). PNMR
3
3
2
2
3
2
СР
.31 s (3H, CH СN), 2.56 q (2H, CH CH , J = 7.5 Hz),
3 3 2 HH
3
3
.89 d (6H, POCH , J = 11.6 Hz), 7.68 d (1H,CH=CP,
JHP = 7.8 Hz). C NMR spectrum (CDCl ), δ , ppm:
3 HP
1
3
13
3
С
3
31
1
СР
1
5
2.66 (CH СН ), 19.17 (СН СN), 21.38 (CH CH ),
3 2 3 3 2
2
spectrum (CDCl ): δ 4.47 ppm.
3 P
4.33 d (POCH , J = 6.2 Hz), 118.89 (C–С=О), 126.12
d (CH=CP, J = 13.8 Hz), 126.75 d (CH=CP, J
25.8 Hz), 158.58 (CH СN), 158.77 d (N=CS, J
0.3 Hz), 158.84 (C=O). P NMR spectrum (CDCl3):
3
СР
2
1
=
=
Diethyl (7-methyl-5-oxo-6-propyl-5H-thia-
zolo[3,2-a]pyrimidin-3-yl)phosphonate (5h). Yield
83%, pale yellow crystals, mp 95°С. H NMR spectrum
(CDCl ), δ, ppm: 0.93 t (3H, CH СН , J = 7.3 Hz),
.47 t (6H, POСН CH , J = 7.1 Hz), 1.47 sext (2H,
СР
СР
3
2
1
3
СР
3
1
1
3
δР 4.36 ppm.
3
3
2
HH
3
1
Diethyl (6-ethyl-7-methyl-5-oxo-5H-thiazolo[3,2-a]-
pyrimidin-3-yl)phosphonate (5e). Yield 79%, pale
yellow crystals, mp 78°С. H NMR spectrum (CDCl ),
δ, ppm: 1.14 t (3H, CH СН , J = 7.5 Hz), 1.40 t (6H,
POСН CH , J = 7.1 Hz), 2.39 s (3H, CH СN), 2.65 q
2H, CH CH , J = 7.5 Hz), 4.38 d. q (4H, POСН ,
2 3 HH
3
CH CH CH , J = 7.3 Hz), 2.32 s (CH СN), 2.48 t
3
2
2
HH
3
3
1
(2H, CH CH CH , J = 7.3 Hz), 4.20 d. q (4H, POСН ,
2
2
3
HH
2
3
3
3
3
3
JHH = 7.1, J = 14.2 Hz), 8.07 d (1H, CH=CP, J
=
HP
HP
3
2
HH
3
3
7
(
.6 Hz). 1 C NMR spectrum (CDCl ), δ , ppm: 14.40
3
С
2
3
HH
3
3
3
CH СН ), 16.65 d (POСН CH , J = 6.2 Hz), 21.61
(СН3СN), 21.84 (CH3CH2CH2), 27.79 (CH3CH2CH2),
(
3 2 2 3 СР
3
2
HH
2
=
3
3
3
JHH = 7.1, J = 14.1 Hz), 7.70 d (1H, CH=CP, JHP
HP
.7 Hz). 13C NMR spectrum (CDCl ), δ , ppm: 12.74
2
7
(
(
6
1
63.71 d (POCH2, JСР = 6.1 Hz), 116.41 (C–С=О), 126.92 d
3
С
3
1
2
CH СН ), 16.45 d (POСН CH , J = 6.6 Hz), 19.29
СН СN), 21.40 (CH CH ), 63.93 d (POCH , J
.2 Hz), 119.05 (C–С=О), 125.41 d (CH=CP, J
3.6 Hz), 128.15 d (CH=CP, J = 223.3 Hz), 158.61
(CH=CP, J = 216.7 Hz), 126.94 d (CH=CP, J
=
3
2
2
3
СР
СР
СР
2
=
=
16.4 Hz), 158.45 (CH СN), 159.18 (C=O), 159.83 d
(N=CS, J = 9.5 Hz). P NMR spectrum (CDCl ): δ
СР 3 Р
3
3
2
2
СР
3
31
2
3
СР
1
1.28 ppm.
СР
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 11 2020