Synthesis of some new 1,2,3,4-tetrahydropyrimidine-2-thiones and their thiazolo[3,2-α]pyrimidine derivatives as potential biological agents

Article abstract of DOI:10.1080/10426500701796330

Some new N-(4-chlorophenyl)-6-methyl-4-aryl-2-thioxo-1,2,3,4-tetrahydro pyrimidine-5-carboxamide 4(a-h) were synthesized by the reaction of N-(4-chlorophenyl)-3-oxobutanamide, thiourea and different aromatic aldehydes. The synthesis of N-(4-chlorophenyl)-7-methyl-5-aryl-2,3-dihydro-5H-thiazolol[3, 2-a]pyrimidine-6-carboxamide 5(a-h) was accomplished by cyclocondensation of 1,2,3,4-tetrahydropyrimidine-2-thiones 4(a-h) and 1,2-dibromoethane. The structures of these compounds have been proved by IR, 1H-NMR, and Mass spectral studies. Synthesized compounds 4(a-h) and 5(a-h) were evaluated for their antimicrobial activities. Some of the compounds exhibited significant inhibition on bacterial and fungal growth as compared to standard drugs. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500701796330

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Phosphorus, Sulfur, and Silicon
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Synthesis of Some New 1,2,3,4-
Tetrahydropyrimidine-2-
thiones and Their Thiazolo[3,2-
a]pyrimidine Derivatives as
Potential Biological Agents
J. D. Akbari a , P. K. Kachhadia a , S. D. Tala a , A.
H. Bapodra a , M. F. Dhaduk a , H. S. Joshi a , K. B.
Mehta b & S. J. Pathak b
a Department of Chemistry, Saurashtra University,
Rajkot, Gujarat, India
b Department of Bioscience, Saurashtra University,
Rajkot, India
Version of record first published: 28 Jul 2008.
To cite this article: J. D. Akbari , P. K. Kachhadia , S. D. Tala , A. H. Bapodra ,
M. F. Dhaduk , H. S. Joshi , K. B. Mehta & S. J. Pathak (2008): Synthesis of Some
New 1,2,3,4-Tetrahydropyrimidine-2- thiones and Their Thiazolo[3,2-a]pyrimidine
Derivatives as Potential Biological Agents, Phosphorus, Sulfur, and Silicon and the
Related Elements, 183:8, 1911-1922
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Phosphorus, Sulfur, and Silicon, 183:1911–1922, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701796330
Synthesis of Some New 1,2,3,4-Tetrahydropyrimidine-2-
thiones and Their Thiazolo[3,2-a]pyrimidine Derivatives
as Potential Biological Agents
J. D. Akbari,1 P. K. Kachhadia,1 S. D. Tala,1 A. H. Bapodra,1
M. F. Dhaduk,1 H. S. Joshi,1 K. B. Mehta,2
and S. J. Pathak2
1Department of Chemistry, Saurashtra University, Rajkot,
Gujarat, India
2Department of Bioscience, Saurashtra University, Rajkot, India
Some
new
N-(4-chlorophenyl)-6-methyl-4-aryl-2-thioxo-1,2,3,4-tetrahydro
pyrimidine-5-carboxamide 4(a–h) were synthesized by the reaction of N-(4-
chlorophenyl)-3-oxobutanamide, thiourea and different aromatic aldehydes. The
synthesis of N-(4-chlorophenyl)-7-methyl-5-aryl-2,3-dihydro-5H-thiazolol[3,2-
a]pyrimidine-6-carboxamide 5(a–h) was accomplished by cyclocondensation
of 1,2,3,4-tetrahydropyrimidine-2-thiones 4(a–h) and 1,2-dibromoethane. The
structures of these compounds have been proved by IR, 1H-NMR, and Mass spectral
studies. Synthesized compounds 4(a–h) and 5(a–h) were evaluated for their
antimicrobial activities. Some of the compounds exhibited significant inhibition
on bacterial and fungal growth as compared to standard drugs.
Keywords 1,2,3,4-Tetrahydropyrimidine-2-thiones; antimicrobial activity; spectral
analysis; synthesis; thiazolo[3,2-a]pyrimidines
INTRODUCTION
The chemistry and the synthesis of 1,2,3,4-tetrahydropyrimidine-2-
thiones have been attracting widespread attention in recent years.
The present popularity of these tetrahydropyrimidines is mainly due
to their close structural relationship to the clinically important dihy-
dropyridine calcium channel blockers.1–6 1,2,3,4-tetrahydropyrimidine-
2-thione is known as a versatile heterocyclic compound which has been
Received 3 August 2007; accepted 1 September 2007.
We are thankful to the Department of Chemistry, Saurashtra University, Rajkot, for
providing the facilities and the Department of Biochemistry, for antimicrobial evaluation.
We are also thankful to CIL, SAIF, Chandigarh, for providing 1H NMR spectral analyses
of compounds.
Address correspondence to Dr. H. S. Joshi, Department of Chemistry, Saurashtra
University, Rajkot-360005, Gujarat, India. E-mail: drhsjoshi49@gmail.com
1911

1912
J. D. Akbari et al.
subjected to a large variety of structural modifications in order to syn-
thesize derivatives with different biological properties. Their various
condensed derivatives are reported to possess calcium antagonist,7–9
anti-inflammatory,10–12 analgesic,13 antitumor,14,15 antidepressant,16
antibacterial, and antifungal effects.17–19 Several synthetic approaches
have been reported for the synthesis of fused heterocyclic pyrimidine
derivatives.20–22
Encouraged by this reports, in this study, synthesis and struc-
tural elucidation of N-(4-chlorophenyl)-6-methyl-4-aryl-2-thioxo-1,2,3,
4-tetrahydropyrimidine-5-carboxamide 4(a–h) and N-(4-chloro-
phenyl)-7-methyl-5-aryl-2,3-dihydro-5H-thiazolol[3,2-a]pyrimidine-6-
carboxamide 5(a–h) are reported. The antibacterial activity against
Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC
12228, Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC
1539, and antifungal activity against Candida albicans ATCC 10231
were investigated.
RESULTS AND DISCUSSION
Chemistry
Ethylacetoacetate suspended in toluene was refluxed with 4-
chloroaniline in presence of catalytic amount of NaOH to give
N-(4-chlorophenyl)-3-oxobutanamide 1. IR spectrum displayed a
definite absorption at 1690 cm−1 due to carboxamide group. Reac-
tion of this with different aromatic aldehyde and thiourea using
classical Biginelli reaction23 yielded N-(4-chlorophenyl)-6-methyl-
4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 4(a–h).
Condensation of 4(a–h) with 1,2-dibromoethane in DMF led to
the N-(4-chlorophenyl)-7-methyl-5-aryl-2,3-dihydro-5H-thiazolol[3,2-
a]pyrimidine-6-carboxamide 5(a–h). The formulas of the compounds
4(a–h) and 5(a–h) were confirmed by the elemental analysis and their
structures were determined by IR, 1H NMR and EIMS spectral data.
The IR spectra of the compounds displayed the characteristics –C=O
stretching vibration at 1720–1660 cm−1. 1H NMR spectrum of the com-
pounds 4c showed a broad singlet at 9.82 ppm due to –NH of carbox-
amide group and two broad singlets at 8.45 and 9.56 ppm due to –NH
group of pyrimidine ring. At 5.44 ppm, a singlet appeared, due to the
chiral proton of the fourth position. Therefore, the above discussion has
supported the pyrimidine ring formation.
In compound 5c, the absence of two broad singlet signals between
8–10 ppm and the presence of four multiplate signals between 3.08–
3.26 ppm have proven that the ring formation took place between the

1913

1914
J. D. Akbari et al.
second and third positions of pyrimidine ring. The formation of com-
pound 5c was further supported by disappearance of the IR band
at 1211 cm−1 due to the C=S group and appearance of a new band
at 680 cm−1 due to the C-S-C bond. EIMS of all compounds were
taken. MS of all compounds showed the molecular ion peak (M+) with
low intensity and other peak due to fragments that supported ex-
pected structures. Experiments were performed to evaluate the an-
tibacterial activity against Staphylococcus aureus ATCC 6538, Staphy-
lococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Pseu-
domonas aeruginosa ATCC 1539, and antifungal activity against Can-
dida albicans ATCC 10231 were investigated using the disk diffusion
method (Table I).
Microbiology
The in vitro antimicrobial activity of the synthesized compounds was
tested against S. aureus ATCC 6538, S. epidermidis ATCC 12228,
E. coli ATCC 8739, P. aeruginosa ATCC 1539, and C. albicans ATCC
10231 using the disk diffusion method where each disc contained 200
µg of the tested compound.24
For this method, Mueller-Hinto agar (Difco) was melted at 100◦C and
after cooing to 56◦C, was poured into Petri plates of 9 cm diameter in
quantities of 20 mL, and left on a flat surface to solidify; the surface
of the medium was dried at 37◦C. Then, the cultures of each bacteria
and yeast strain—after being kept in Mueller-Hinton broth at 37◦C for
18–24 h and diluted with Mueller-Hinton broth to 105 cfu/mL—were
pipetted into the Mueller-Hinton agar plate prepared as described pre-
viously. The surface of the medium was allowed to dry. The 10000 µg/mL
(in DMSO) compound impregnated discs were applied to the surface of
inoculated plates. The Petri plates were placed in an incubator at 37◦C.
After 10–24 h of incubation, the Petri plates were examined. Evaluation
of the new compounds established that compound 4e in which a nitro
group is present at the third position of the aryl ring, possess stronger
antibacterial activity as compared to others. While compounds 4b, 4c,
and 4e were active against S. epidermidis ATCC 12228; 4b, 4e, and
4f were active against E. coli ATCC 8739; and 4e was active against
P. aeruginosa ATCC 1539. In case of C. albicans ATCC 10231 com-
pounds 4e and 5e showed a better activity than the others. Compounds
4a, 4b, 4f, 4g, 4h, 5c, and 5e exhibited moderate activities as compared
to the standard against various microorganisms. It was also noticed
that compounds 4(a–h) demonstrated higher inhibitory activity than
5(a–h) due to its free –C=S group (Table II).

1915

1916
J. D. Akbari et al.
SCHEME 1
EXPERIMENTAL SECTION
General Procedures
Melting points were estimated in open capillaries and are uncorrected.
Elemental analyses were performed on a Carlo Erba EA 1108 elemental
analyzer. IR spectra were recorded on KBr discs, using an FTIR-8400
Spectrophotometer. 1H NMR spectra were taken on a Bruker AVANCE
II 400 (1H: 400 Mz, [d6] DMSO) Spectrometer. Mass spectra were deter-
mined using direct inlet probe on a GCMS-QP2010 mass spectrometer
(Shimadzu). Reactions were monitored on Merck aluminum thin layer
chromatography (TLC, UV254nm) pates. Visualization was accomplished
either on UV chamber or in Iodine vapor. Column chromatography was
carried out on silica gel (60–120 mesh, Merck chemicals).
Synthesis of N-(4-chlorophenyl)-3-oxobutanamide (1)
A suspension of ethylacetoacetate (0.01 mol) and 4-choloro aniline (0.01
mol) in toluene (50 ml) containing catalytic amount (0.05 ml, 40%) of
NaOH was reflux on oil bath for 8 h. After completion of the reaction
(TLC monitoring), the solvent was removed under reduced pressure,
separated solid was filtered, washed with petroleum ether and crystal-
lized from ethanol to give 1.
General procedure of synthesis of N-(4-chlorophenyl)-6-
methyl-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-
carboxamide (4a–h)
A mixture of N-(4-chlorophenyl)-3-oxobutanamide (0.01 mol), differ-
ent aromatic aldehyde (0.01 mol), thiourea (0.01 mol), and ethanol
(8 ml), containing 0.4 ml of concentrated HCl was heated under re-
flux for 6–8 h. The solution was allowed to stand at −20◦C for several

Thiones and Thiazolo Pyrimidine Derivatives
1917
hours and precipitation was observed. The products were isolated as
crystalline powder 4a–h.
N-(4-chlorophenyl)-6-methyl-4-(3,4-dimethoxyphenyl)-2-
thioxo-1,2,3,4-tetrahyd-ropyrimidine-5-carboxamide (4a)
IR (νmax cm−1, KBr): 3368 (N-H str.), 1678 (C=O str.), 1215 (C=S str.),
765 (C-Cl str.). 1H NMR 400 Mz (CDCl3+ DMSO d6): 2.14 (s, 3H, -CH3),
3.75 (s, 3H, -OCH3), 3.78 (s, 3H, -OCH3, 5.45 (s, 1H, Ar-Hc), 6.81–6.90
(m, 3H, Ar-H), 7.18–7.20(d, 2H, Ar-Hb-b’ J = 8.44Hz), 7.56–7.58(d, 2H,
Ar-Ha-a’ J = 8.48Hz) 9.24(s, 1H, -NH pyrimidine), 9.60 (s, 1H, -NH
pyrimidine), 9.80 (s, 1H, -NH amide). EI+ m/z: 419 (M+2), 417, 402,
386, 357, 291, 259, 232, 208, 191, 176, 153, 127.
N-(4-chlorophenyl)-6-methyl-4-(4-methoxyphenyl)-2-thioxo-
1,2,3,4-tetrahydro-pyrimidine-5-carboxamide (4b)
IR (νmax cm−1, KBr): 3396 (N-H str.), 1683 (C=O str.) 1213 (C=S str.),
756 (C-Cl str.). 1H NMR 400 Mz (CDCl3+ DMSO d6): 2.13 (s, 3H, -CH3),
3.74 (s, 3H, -OCH3), 5.43 (s, 1H, Ar-Hc), 6.81–6.64 (dd, 2H, Ar-Hf-f’ J
= 11.44Hz), 7.16–7.20 (d, 2H, Ar-Hb-b’ J = 7.12Hz), 7.22–7.27(dd, 2H,
Ar-He-e’ J = 11.8Hz), 7.53–7.57(dd, 2H, Ar-Ha-a’ J = 7.04Hz) 9.23(s,
1H, -NH pyrimidine), 9.56 (s, 1H, -NH pyrimidine), 9.83 (s, 1H, -NH
amide). EI+ m/z: 387, 357, 261, 233, 202, 178, 161, 153, 127, 90, 67.
N-(4-chlorophenyl)-6-methyl-4-(2-methoxyphenyl)-2-thioxo-
1,2,3,4-tetrahydro-pyrimidine-5-carboxamide (4c)
IR (νmax cm−1, KBr): 3383 (N-H str.), 1683 (C=O str.) 1211 (C=S str.),
732 (C-Cl str.). 1H NMR 400 Mz (CDCl3+ DMSO d6): 2.14 (s, 3H, -CH3),
3.74 (s, 3H, -OCH3), 5.44 (s, 1H, Hc), 6.87–7.59 (m, 8H, Ar-H, J = 7.6Hz),
8.45 (s, 1H, -NH pyrimidine), 9.56 (s, 1H, -NH pyrimidine), 9.82 (s, 1H,
-NH amide). EI+ m/z: 387, 356, 261, 233, 202, 178, 155, 136, 91, 67.
N-(4-chlorophenyl)-6-methyl-4-phenyl-2-thioxo-1,2,3,4-
tetrahydropyrimidine-5-carboxamide (4d)
IR (νmax cm−1, KBr): 3376 (N-H str.), 1704 (C=O str.) 1211 (C=S
str.), 743 (C-Cl str.). 1H NMR 400 Mz (CDCl3+ DMSO d6): 2.14 (s, 3H,
-CH3), 5.50 (s, 1H, Ar-Hc), 7.17–7.19(dd, 2H, Ar-Hb-b’ J = 6.92Hz),
7.20–7.34(m, 5H, Ar-H), 7.53–7.57(dd, 2H, Ar-Ha-a’ J = 6.96Hz), 9.22
(s, 1H, -NH pyrimidine), 9.5636 (s, 1H, -NH pyrimidine), 9.85 (s, 1H,
-NH amide). EI+ m/z: 357, 342, 280, 231, 216, 172, 144, 131, 103, 91,
67.

1918
J. D. Akbari et al.
Where R = 3,4-(OCH3)2, 4-OCH3, 2-OCH3, 3-NO2, 3-OH, 2-OH, 2-Cl
SCHEME 2
N-(4-chlorophenyl)-6-methyls-4-(3-nitrophenyl)-2-thioxo-
1,2,3,4-tetrahydropyri-midine-5-carboxamide (4e)
IR (νmax cm−1, KBr): 3408 (N-H str.), 1683 (C=O str.) 1218 (C=S str.),
736 (C-Cl str.)1H NMR 400 Mz (CDCl3+ DMSO d6): 2.20 (s, 3H, -CH3),
5.59 (s, 1H, Ha), 7.17–8.25 (m, 8H, Ar-H, J = 6.96Hz), 9.51 (s, 1H, -NH
pyrimidine), 9.72 (s, 1H, -NH pyrimidine), 10.87 (s, 1H, -NH amide).
EI+ m/z: 402, 385, 357, 276, 217, 176, 153, 127, 102, 90, 67.
N-(4-chlorophenyl)-6-methyl-4-(3-hydroxyphenyl)-2-thioxo-
1,2,3,4-tetrahydropy-rimidine-5-carboxamide (4f)
IR (νmax cm−1, KBr): 3406 (N-H str.), 1718 (C=O str.) 1210 (C=S str.),
744 (C-Cl str.). 1H NMR 400 Mz (CDCl3+ DMSO d6): 2.15 (s, 3H, -CH3),
5.44 (s, 1H, Ar-Hc), 6.72–7.14 (m, 4H, Ar-H), 7.16–7.20 (dd, 2H, Ar-Hb-
b’ J = 6.96Hz), 7.47–7.52 (dd, 2H, Ar-Hb-b’ J = 7.04Hz) 8.78 (s, 1H, -NH
pyrimidine), 9.11 (s, 1H, -NH pyrimidine), 9.46 (s, 1H, -NH amide). EI+
m/z: 373, 313, 247, 220, 188, 160, 147, 127, 99, 91, 65.

Thiones and Thiazolo Pyrimidine Derivatives
1919
N-(4-chlorophenyl)-6-methyl-4-(2-hydroxyphenyl)-2-thioxo-
1,2,3,4-tetrahydrop-yrimidine-5-carboxamide (4g)
IR (νmax cm−1, KBr): 3406 (N-H str.), 1718 (C=O str.) 1210 (C=S
str.), 723 (C-Cl str.). 1H NMR 400 Mz (CDCl3+ DMSO d6): 1.81 (s, 3H,
-CH3), 4.65 (s, 1H, Ar-Hc), 6.77–7.62 (m, 8H, Ar-H), 9.97 (s, 1H, -NH
pyrimidine), 9.05 (s, 1H, -NH pyrimidine), 10.22 (s, 1H, -NH amide).
EI+ m/z: 373, 247, 221, 188, 160, 147, 127, 91, 65.
N-(4-chlorophenyl)-6-methyl-4-(2-chlorophenyl)-2-thioxo-
1,2,3,4-tetrahydropy-rimidine-5-carboxamide (4h)
IR (νmax cm−1, KBr): 3403 (N-H str.), 1702 (C=O str.) 1214 (C=S str.),
743 (C-Cl str.). 1H NMR 400 Mz (CDCl3+ DMSO d6): 2.19 (s, 3H, -CH3),
5.92 (s, 1H, Ha), 7.15–7.59 (m, 8H, Ar-H), 8.50 (s, 1H, -NH pyrimidine),
9.48 (s, 1H, -NH pyrimidine), 9.79 (s, 1H, -NH amide). EI+ m/z: 393,
391, 356, 267, 265, 229, 206, 165, 143, 127, 101, 90, 67.
General Procedure of Synthesis of N-(4-chlorophenyl)-7-
methyl-5-aryl-2,3-dihydro-5H-thiazolol[3,2-a]pyrimidine-6-
carboxamide 5(a–h)
1,2-Dibromoethane (0.01 mol) was added to a boiling solution of 1,2,3,4-
tetrahydropyrimidine-2-thiones (0.01 mol) in dimethyl formamide
(5 ml) and then refluxed for 45 min. The resulting solution was al-
lowed to stand at room temperature, and the precipitated mineral salts
were isolated by filtered through a Buchner funnel. The residue was
triturated with sodium bicarbonate solution followed by ethanol and
purified by column chromatography (Silica gel, hexane/ethyl acetate
7:3) to give analytical grade pure products 5(a–h).
N-(4-chlorophenyl)-7-methyl-5-(3,4-dimethoxyphenyl)-2,3-
dihydro-5H-thiazolol-[3,2-a]-pyrimidine-6-carboxamide (5a)
IR (νmax cm−1, KBr): 3420 (N-H str.), 1706 (C=O str.). 684 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.22 (s, 3H, -CH3), 3.16–3.58 (m,
4H, CH2-CH2), 3.80 (s, 3H, -OCH3), 3.82 (s, 3H, -OCH3), 5.58 (s, 1H,
Ar-Hc), 6.98–7.44 (m, 7H, Ar-H), 9.03 (S, 1H, NH-amide). EI+ m/z: 443,
317, 413, 398, 287, 275, 244, 159, 153, 127, 115, 86.
N-(4-chlorophenyl)-7-methyl-5-(4-methoxyphenyl)-2,3-
dihydro-5H-thiazolol[3,2-a]-pyrimidine-6-carboxamide (5b)
IR (νmax cm−1, KBr): 3378 (N-H str.), 1698 (C=O str.), 678 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.16 (s, 3H, -CH3), 3.12–3.46 (m,
4H, CH2-CH2), 3.80 (s, 3H, -OCH3), 5.45 (s, 1H, Ar-Hc), 6.87–7.52 (m,

1920
J. D. Akbari et al.
9H, Ar-H). EI+ m/z: 413, 398, 287, 275, 259, 244, 185, 159, 153, 127,
115, 86, 67.
N-(4-chlorophenyl)-7-methyl-5-(2-methoxyphenyl)-2,3-
dihydro-5H-thiazolol[3,2-a]-pyrimidine-6-carboxamide (5c)
IR (νmax cm−1, KBr): 3401 (N-H str.), 1707 (C=O str.), 680 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.31 (s, 3H, -CH3), 3.08–3.26 (m,
4H, CH2-CH2), 3.85 (s, 3H, -OCH3), 5.96 (s, 1H, Ar-Hc), 6.90–7.47 (m,
9H, Ar-H). EI+ m/z: 413, 398, 287, 259, 243, 181, 159, 153, 127, 115, 86,
67.
N-(4-chlorophenyl)-7-methyl-5-phenyl-2,3-dihydro-5H-
thiazolol[3,2-]pyrimidine-6-carboxamide (5d)
IR (νmax cm−1, KBr): 3397 (N-H str.), 1710 (C=O str.), 682 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.14 (s, 3H, -CH3), 3.18–3.67 (m,
4H, CH2-CH2), 5.60 (s, 1H, Ha), 7.06–7.52 (m, 9H, Ar-H), 9.03 (s, 1H,
-NH amide). EI+ m/z: 383, 368, 306, 257, 242, 179, 155, 127, 115, 86,
67.
N-(4-chlorophenyl)-7-methyl-5-(3-nitorphenyl)-2,3-dihydro-5H-
thiazolol[3,2-a]-pyrimi-dine-6-carboxamide (5e)
IR (νmax cm−1, KBr): 3388 (N-H str.), 1704 (C=O str.), 680 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.24 (s, 3H, -CH3), 3.22–3.47 (m,
4H, CH2-CH2), 5.71 (s, 1H, Ar-Hc), 7.21–8.23 (m, 9H, Ar-H). EI+ m/z:
428, 399, 302, 275, 243, 228, 153, 127, 115, 86, 67.
N-(4-chlorophenyl)-7-methyl-5-(3-hydroxyphenyl)-2,3-dihydro-
5H-thiazolol[3,2-a]-pyrimidine-6-carboxamide (5f)
IR (νmax cm−1, KBr): 3367 (N-H str.), 1677 (C=O str.), 687 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.20 (s, 3H, -CH3), 3.18–3.66 (m,
4H, CH2-CH2), 5.53 (s, 1H, Ar-Hc), 6.67–7.56 (m, 8H, Ar-H), 9.43 (s, 1H,
-OH amide), 9.49 (s, 1H, -NH amide). EI+ m/z: 399, 384, 306, 273, 245,
171, 153, 127, 115, 86, 67.
N-(4-chlorophenyl)-7-methyl-5-(2-hydroxyphenyl)-2,3-dihydro-
5H-thiazolol[3,2-a]-pyrimidine-6-carboxamide (5g)
IR (νmax cm−1, KBr): 3377 (N-H str.), 1688 (C=O str.), 685 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.26 (s, 3H, -CH3), 3.19–3.63 (m,
4H, CH2-CH2), 4.88 (s, 1H, Ar-Hc), 6.87–7.65 (m, 8H, Ar-H), 10.29 (s,
1H, -OH amide), 10.32 (s, 1H, -NH amide). EI+ m/z: 399, 385, 303, 272,
245, 171, 153, 127, 115, 86, 67.

Thiones and Thiazolo Pyrimidine Derivatives
1921
N-(4-chlorophenyl)-7-methyl-5-(2-chlorophenyl)-2,3-dihydro-
5H-thiazolol[3,2-a]-pyrim-idine-6-carboxamide (5h)
IR (νmax cm−1, KBr): 3398 (N-H str.), 1706 (C=O str.), 683 (C-S-C str.).
1H NMR 400 Mz (CDCl3+ DMSO d6): 2.19 (s, 3H, -CH3), 3.12–3.64 (m,
4H, CH2-CH2), 5.53 (s, 1H, Ar-Hc), 7.19–7.36 (m, 10H, Ar-H). EI+ m/z:
417, 402, 291, 276, 263, 227, 189, 153, 127, 99, 86, 67.
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