Synthesis of 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4- triazole-3-thione and its reactions with C-electrophiles

Article abstract of DOI:10.1007/s10593-007-0145-3

4-Amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2, 4-trazole-3-thione is formed from the reaction of 4,6- diphenylpyrimidinecarboxylic acid or its ethyl ester with thiocarbonyl hydrazide. Alkylation of the product leads to S-alkyl derivaties or 6-substituted 3-(4,6-diphenyl-2-pyriimidinyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4- thiadiazine. Acetylation of 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro- 2H-1,2,4-triazole-3-thione gave under different conditions monoacetyl-, diacetyl, and triacetyl derivatives at the amino group and the N₍₂₎ atom, whereas benzoylation gave a benzoyl group at the amino group and 3-(4,6-diphenyl-2-pyrimidinyl)-6-phenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole.

Full text of DOI:10.1007/s10593-007-0145-3

Chemistry of Heterocyclic Compounds, Vol. 43, No. 7, 2007
SYNTHESIS OF 4-AMINO-5-(4,6-DIPHENYL-
2-PYRIMIDINYL)-3,4-DIHYDRO-2H-
1,2,4-TRIAZOLE-3-THIONE AND ITS
REACTIONS WITH C-ELECTROPHILES
G. Mekuškiene and P. Vainilavičius
4-Amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-trazole-3-thione is formed from the
reaction of 4,6-diphenylpyrimidinecarboxylic acid or its ethyl ester with thiocarbonyl hydrazide.
Alkylation of the product leads to S-alkyl derivaties or 6-substituted 3-(4,6-diphenyl-2-pyriimidinyl)-7H-
1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine. Acetylation of 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-
2H-1,2,4-triazole-3-thione gave under different conditions monoacetyl-, diacetyl, and triacetyl derivatives
at the at the amino group and the N(2) atom, whereas benzoylation gave a benzoyl group at the amino
group and 3-(4,6-diphenyl-2-pyrimidinyl)-6-phenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole.
Keywords: 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-trazol-3-thione, alkylation,
acylation, heterocyclization.
5-Substituted 4-amino-1,2,4-triazole-3-thiones and their S-alkylated and condensed derivatives possess
antimicrobial [1-6] and anti-inflammatory activity [7-9]. 5-(4,6-Diphenyl-2-pyrimidinyl))-3,4-dihydro-2H-1,2,4-
triazole-3-thione and its 4-phenyl derivative, which we synthesized earlier, show anti-inflammatory activity [10,
11]. In a continuation of our investigation of a series of pyrimidinyltriazole, we describe in this paper the
synthesis of 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-thione (1) and its reactions
with C-electrophiles.
We previously prepared thione 1 from 5-(4,6-diphenyl-2-pyrimidinyl)-1,3,4-oxadiazole-2-thione [11]
and hydrazine hydrate in boiling absolute butanol in 60% yield [12]. In the present work we studied a shorter
method for the synthesis of 1 by fusing 4,6-diphenyl-2-pyrimidinecarboxylic acid with thiocarbohydrazide [13]
at the melting point of the acid or the reaction of ethyl 4,6-diphenyl-2-pyrimidinecarboxylate [14] and
thiocarbohydrazide in boiling absolute methanol in the presence of sodium methoxide. However, the yields of
the desired product were lower in both cases (42 and 33% respectively).
Reaction of thione 1 with iodomethane in absolute ethanol gave the methylsulfanyl derivative 2.
Reaction of thione 1 with ω-bromoacetophenone and ethyl 4-chloroacetate was apparently accompanied by
cyclocondensation of the S-alkylated intermediate with the formation of 6-substituted 3-(4,6-diphenyl-
2-pyrimidinyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines 3a,b.
__________________________________________________________________________________________
Vilnius University, Vilnius 01513, Lithuania; e-mail: giedrute.mekuskiene@chf.vu.lt. Translated from
Khimiya Geterotsiklicheskikh Soedinenii, No. 7, 1088-1094, July, 2007. Original article submitted February 27,
2006.
0009-3122/07/4307-0919©2007 Springer Science+Business Media, Inc.
919

RCO2H
RCO2Et
(NH2NH)2CS
NH2
(NH2NH)2CS
R
N
MeONa
S
N
N
H
1
1. BrCH2COPh
MeI
2. ClCH2COCH2CO2Et
N
N
R
BrCH2CO2Et
R
N
R1
N
S
N
H2N
N
Me
N
N
N
R
2
S
N
S
3 a,b
O
PhNCS
H2N
5
OEt
H
H
N
N
R
Ph
MeONa,
MeOH
N
S
N
R
N
H
N
SMe
O
N
4
N
N
S
6
R = 4,6-diphenyl-2-pyrimidinyl; 3 а R1 = Ph, b R1 = CH2CO2Et
Compound 2 reacts with phenyl isothiocyanate in absolute pyridine at room temperature to give the
N-thioureido derivative 4. Compound 5, the product of S-alkylation of thione 1 with ethyl bromoacetate,
cyclized to 1,2,4-triazolo[3,4-b]thiadiazin-6-one 6 on treatment with sodium methoxide in boiling methanol.
1
AcBr
Ac2O
N
Ac2
S
AcOH
Py
Ac2O
R
N
Ac
S
NH
R
N
N
N
H
N
N
H
9
Ac2
N
7
R
N
S
N
N
Ac
8
R = 4,6-diphenyl-2-pyrimidinyl
920

Table 1. Characteristics of the Compounds Synthesized, 2-12
Found, %
——————
Calculated, %
Com-
pound
Empirical
formula
mp, °С*
Yield, %
С
Н
N
2
C19H16N6S
63.22
63.31
70.20
69.94
63.41
63.14
62.92
63.01
61.36
61.10
62.50
62.16
61.25
61.84
61.26
61.00
61.70
61.38
66.39
66.65
69.33
69.42
62.68
62.67
4.22
4.47
4.25
4.06
4.66
4.42
4.46
4.27
4.66
4.66
3.64
3.65
4.27
4.15
4.17
4.27
4.36
4.21
3.88
4.03
3.98
3.73
4.67
4.51
23.21
23.32
19.05
18.82
18.32
18.41
19.70
19.78
19.65
19.43
21.66
21.75
21.78
21.63
17.90
17.79
19.48
19.52
18.54
18.65
19.67
19.43
20.82
20.88
242-243
260.0-261.5
178.0-178.5
161-162
65
63
47
71
87
46
51
70
27
51
66
35
3a
3b
4
C26H18N6S
C24H20N6O2S
C26H21N7S2
C22H20N6O2S
C20H14N6OS
C20H16N6OS
C24H20N6O3S
C22H18N6O2S
C25H18N6OS
C25H16N6S
5
179-180
6
272-273
7
182 (dec.)
231-232
8
9
158-159
10
11
12
>300 (dec.)
>300 (dec.)
159-160
C21H18N6ОS
_______
* Solvent: MeOH (compound 2), MeCN (compounds 3a, 5, 8), EtOH
(compounds 3b, 7, 10, 12), dioxan (compounds 6, 9), DMF (compound
11).
Acetylation of thione 1 with acetic anhydride and acetyl bromide proceeded with participation of the
amino group and the N(2) atom of the triazole ring.
An equivalent amount of acetic anhydride selectively acylated the amino group to form the monoacetyl
derivative 7; an excess of acetic anhydride acylated the amino group and the atom N(2) of the triazole ring to give
the triacetyl derivative 8. On boiling equivalent amounts of the thione 1 and acetyl bromide in absolute pyridine
for 1 h, the diacetyl derivative 9 was isolated.
When thione 1 was boiled for a short time (0.5 h) with benzoic acid in the presence of phosphorus
oxychloride the (10) benzoyl derivative was formed. When the reaction time was increased to 5 h the 1,2,4-
triazolo[4,3-b]-1,3,4- thiadiazole heterocyclic system 11 was produced.
When thione 1 was boiled with ethyl orthoformate the ethoxymethylenamine derivative 12 was formed.
According to the 1H NMR spectra a mixture of two geometric isomers in the ratio 7:1 was formed.
The structures of the compounds synthesized were confirmed by the results of elemental analysis
(Table 1) and IR and 1H NMR spectroscopic (Table 2).
In the IR spectra absorption bands of the C=O of esters are present of alkylated compounds 3b and 5 at
1721 and 1728, the amide group of the condensed thiadiazinone 6 at 1703, and the acyl groups of monoacetyl
(7) and benzoyl (10) derivatives at 1691 and 1692, triacetyl (8) and diacetyl (9) derivatives at 1753, 1728, and
1742 cm-1 respectively. The absorptions in derivatives 7-10, 12 in the 1244-1270 cm-1 region are characteristic of
the C=S bond in the triazole ring. In the spectra of the S-alkyl derivatives 2, 4, 5 and the condensed compounds
3a,b and 6 these bands are absent, but the C=S group in the thioureido derivative is observed at 1317 cm-1.
921

Table 2. IR and 1H NMR Spectral Data for Compounds 2-12
IR spectrum,
Com-
pound
1Н NMR spectrum, δ, ppm (J,Hz)*
ν, cm-1
2
3336 (NH),
2.70 (3H, s, CH3); 6.53 (2H, s, NH2);
1584 (C=C),
1572 (C=N)
7.63-7.65 (6Н, m, 3-, 4-, 5-СН, С6Н5);
8.47-8.51 (4Н, m, 2-, 6-CН, С6Н5); 8.71 (1Н, s, CH pyrim.)
3а
3b
4
1585 (С=C),
1574 (С=N)
4.57 (2Н, s, CH2); 7.53-7.63 (9Н, m, 3-, 4-, 5-СН, С6Н5,
3'-, 4'-, 5'-СН, С6Н5); 8.08 (2Н, d, J = 7.0, 2'-, 6'-CНС6Н5);
8.48 (4Н, d, J = 8.1, 2-,6-СН, С6Н5); 8.76 (1Н, s, CH pyrim.)
1728 (С=О),
1584 (С=C),
1573 (С=N)
1.90 (3Н, t, J = 7.0, CH2СН3); 3.89 (2Н, s, СН2); 4.09 (2Н, s, SСН2);
4.16 (2Н, q, J = 7.0, CH2Me); 7.61-7.64 (6Н, m, С6Н5);
8.44-8.46 (4Н, m, С6Н5); 8.74 (1Н, s, CH pyrim.)
3444, 3201 (NH),
1586 (C=C),
1574 (C=N),
1317 (C=S)
2.75 (3H, s, CH3); 7.12-7.57 (11H, m, 3-, 4-, 5-СН, С6Н5,
3'-, 4'-, 5'-СН, С6Н5); 8.47-8.66 (4H, m, 2-, 6-СН, С6Н5);
8.71 (1Н, s, CH pyrim.); 10.9 (1H, s, NH); 11.03 (1H, s, NH)
5
6
7
3425 (NH),
1721 (C=O),
1584 (C=C),
1574 (C=N)
3389 (NH),
1703 (С=О),
1585 (С=C),
1574 (С=N)
1.24 (3H, t, J = 7.0, CH2СН3); 4.17 (2Н, q, J = 7.0, CH2Me);
4.20 (2H, s, SCH2); 6.57 (2H, s, NH2); 7.63-7.65 (6Н, m,
3-, 4-, 5-СН, С6Н5); 8.47-8.50 (4Н, m, 2-, 6-CН, С6Н5);
8.70 (1Н, s, CH pyrim.)
3.98 (2Н, s, CH2); 7.64-7.66 (6Н, m, 3-, 4-, 5-СН, С6Н5);
8.46-8.49 (4Н, m, 2-, 6-CH, С6Н5); 8.73 (1Н, s, CH pyrim.);
12.40 (1Н, br. s, NH)
3448, 3158 (NH),
1691 (C=O),
1264 (C=S)
1.99 (3H, s, CH3); 7.63-7.65 (6Н, m, 3-, 4-, 5-СН, C6H5);
8.46-8.49 (4H, d, J = 9, 2-, 6-CH, С6Н5);
8.74 (1H, s, CH pyrim.); 11.63 (1H, s, NHСОMe);
14.43 (1H, br. s, NH triazole)
8
9
1753, 1728 (C=O),
1576 (С=C), (С=N), 3-, 5-CH, С6Н5); 7.96 (2Н, t, J = 9.0, 4-CH, С6Н5);
1270 (C=S)
2.78 (6H, s, CH3); 3.09 (3H, s, CH3); 7.82 (4H, t, J = 9.0,
8.21 (4Н, d, J = 7.0, 2-, 6-CH, С6Н5); 8,75 (1Н, s, CH pyrim.)
3459 (NH),
1742 (C=O),
1588 (С=C),
1576 (С=N),
1244 (C=S)
2.45 (6H, s, CH3); 7.63-7.65 (6Н, m, 3-, 4-, 5-СН, C6H5);
8.33-8.37 (4H, d, J = 12, 2-, 6-CH, С6Н5);
8.74 (1H, s, CH pyrim.); 14.92 (1H, s, NH triazole)
10
3369, 3154 (NH),
1692 (C=O),
1587 (С=C),
1575 (С=N),
1263 (C=S)
7.43-7.67 (9H, m, 3-, 4-, 5-CH, C6H5); 8.04 (2Н, d, J = 7.0,
2'-, 6'-CH, С6Н5); 8.34 (4Н, d, J = 7.5, 2-, 6-CH, С6Н5);
8.70 (1H, s, CH pyrim.); 12.25 (1H, s, NHCOC6H5);
14.57 (1H, s, NH triazole)
11
12
1582 (С=C),
1573 (C=N)
7.68-7.78 (9H, m, 3-, 4-, 5-CH, C6H5, 3'-, 4'-, 5'-СН, С6Н5);
8.14-8.17 (2Н, m, 2'-, 6'-CН, С6Н5); 8.63-8.66 (4Н, m,
2-, 6-СН, С6Н5); 8.82 (1Н, s, CH pyrim.)
3300 (NH),
1587 (С=C),
1576 (С=N),
1262 (C=S)
0.95, 1.29 (3H, t, J = 7.0, CH2СН3); 4.15, 4.37 (2Н, q,
J = 7.0, CH2Me); 7.63-7.65 (6Н, m, 3-, 4-, 5-СН, С6Н5);
8.48-8.51 (4H, m, 2-, 6-CH, С6Н5); 8.7 (1Н, s, CH pyrim.);
8.77, 8.81 (1Н, s, N=CН); 14.37 (1H, s, NH triazole)
_______
* H pyrim. – proton of the pyrimidine unit. H triazole – proton of the triazole ring.
1
The signal of the H-5 proton of the pyrimidine ring is present at 8.70-8.82 ppm in the H NMR spectra
of compounds 2-12 and the phenyl group of pyrimidine in the intervals 7.12-7.67 and 8.33-8.66 ppm. In the
spectra of compounds 7, 9, 10, and 12 the signal of the proton of the NH group of the triazole ring is observed in
the range 14.37-14.92, while in stronger field the signal of the NH protons of the thioureido derivative 4 (10.9
and 11.03) and the acylated compounds 7 and 10 are observed (11.63 and 12.25 ppm).
922

O
N
HN
N
Ph
R
OEt
BzOH
N
HC(OEt)3
R
1
S
POCl3
0.5 h
N
S
N
H
N
N
H
BzOH,
12
POCl3, 5 h
10
Ph
N
R
N
S
N
N
11
R = 4,6-diphenyl-2-pyrimidyl
EXPERIMENTAL
1H NMR spectra of DMSO-d6 solutions (compound 8 in CF3COOD) with TMS as internal standard were
recorded with Varian Unity Inova (300 MHz) spectrometer. IR spectra of KBr disks were recorded on a Perkin-
Elmer Spectrum BX FT-IR spectrometer. The course of reaction and the purity of compounds 2-6 were
monitored by TLC on Silufol UV-254 (Kavalier) plates with eluents: ethyl acetate (for 2,4), 1:3 ethyl acetate–
ether (for 3b, 5, 6), 1:2 ethyl acetate–ether (for 12), and 1:1 ethyl acetate–ethanol (for 3a). Alugram® SIL G/UV-
254 (Macherey-Nagel) plates were used for compounds 7-10, eluent 4:1 ethyl acetate-methanol (for compound
10 2:1 chloroform-ether).
4-Amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-thione (1). A. A mixture of
4,6-diphenylpyrimidine-2-carboxylic acid (2.76 g, 10 mmol) and thiocarbohydrazide (1.06 g, 10 mmol) was
heated on a Wood's metal bath at 165-170°C for 30 min. After cooling the reaction mass was triturated and
treated with boiling ethanol (10×12 ml). The residue of product 1 was dried and recrystallized. Yield 1.45 g
(42%); mp 244-245°C (DMF-H2O); 244-245°C (DMF-H2O) [11].
B. Thiocarbohydrazide (0.74 g, 6.98 mmol) was added to sodium methoxide (from metallic sodium,
0.107 g, 4.65 mmol) in methanol (10 ml). The suspension was boiled for 15 min, then ethyl 4,6-diphenyl-
pyrimidine-2-carboxylate (1.42 g, 4.65 mmol) was added, and the mixture was boiled for 3 h. Water (10 ml) was
added to the cooled mixture at room temperature and the mixture was acidified to pH 4 with 10% HCl. The
residue of product 1 was filtered off, washed with water, treated with boiling ethanol, dried and recrystallized.
Yield 0.53 g (33 %); mp 244-245°C (DMF-H2O); 244-245°C (DMF-H2O) [11].
5-(4,6-Diphenyl-2-pyrimidinyl)-3-methylsulfanyl-4H-1,2,4-triazole-4-amine (2). Iodomethane (0.25 g,
0.34 ml, 1.728 mmol) was added dropwise and with stirring to a suspension of thione 1 (0.6 g, 1.728 mmol) in
absolute ethanole (40 ml). The reaction mixture was boiled with stirring for 3 h. The solvent was removed with a
rotary evaporator, the solid product was treated with stiring with 10% KOH (15 ml). The solid product 2 was
filtered off, washed with water to neutral reaction with a small amount of methanol, dried and recrystallized.
Ethyl [4-Amino-5-(4,6-diphenyl-2-pyrimidinyl)-4H-1,2,4-triazo-3-ylsulfanyl]acetate (5). Triethyl-
amine (0.15 g, 0.2 ml, 1.443 mmol) was added to a boiling suspension of thione 1 (0.5 g, 1.443 mmol) in
absolute ethanol (10 ml), the mixture was boiled for 5 min and then ethyl bromoacetate (0.24 g, 0.16 ml,
1.443 mmol) was added. The mixture was boiled with stirring for 2 h. The separated product 5 was filtered off
and recrystallized.
923

3-(4,6-Diphenyl-2-pyrimidinyl)-6-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine (3a). A mixture
of thione 1 (0.25 g, 0.721 mmol) and ω-bromoacetophenone (0.14 g, 0.721 mmol) in absolute ethanol (5 ml) was
boiled with stirring for 2 h. The hot solution was filtered, the crystals of product 3a were washed with ethanol
and ether, dried and crystallized. An additional amount of the product was obtained by evaporation of the
filtrate.
Ethyl [3-(4,6-Diphenyl-2-pyrimidinyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine (3b). Ethyl 4-chloro-
acetoacetate (0.24 g, 0.2 ml, 1.443 mmol) was added to a boiling suspension of thione 1 (0.5 g, 1.443 mmol) and
triethylamine (0.15 g, 0.2 ml, 1.443 mmol) in absolute ethanol (40 ml) and the mixture was boiled for 9 h. The hot
solution was filtered, the filtrate was evaporated to 10 ml and cooled. The solid residue of 3b was filtered off and
recrystallized.
N1-[5-(4,6-Diphenyl-2-pyrimidinyl)-3-methylsulfanyl-4H-1,2,4-triazol-4-yl]-N2-phenylthiocarbamide
(4). Compound 2 (0.2 g, 0.333 mmol) was dissolved with stirring in absolute pyridine (4 ml). Phenyl isothiocyanate
(0.054 g, 0.3995 mmol) was added dropwise and the mixture was stirred at room temperature for 4 days. The
reaction mixture was poured into ice water (15 ml) and kept for 1 day. Crystals of 4 were filtered off, washed with
water, dried and recrystallized.
3-(4,6-Diphenyl-2-pyrimidinyl)-6,7-dihydro-5H-1,2,4-triazolo[3,4-b]-1,3,4-thiadazin-6-one (6). A
mixture of compound 5 (0.54 g, 1.25 mml) and sodium methoxide (from 0.03g, 1.25 mmol, sodium) in methanol
(20 ml) was boiled with stirring for 5 h. The reaction mixture was neutralized with dilute HCl (1:1). The
precipitate of product 6 was filtered off, washed with ether, dried, and recrystallized.
N-[5-(4,6-Diphenyl-2-pyrimidinyl)-3-thioxo-1,2,4-triazol-4-yl]acetamide (7). Freshly distilled acetic
anhydride (0.088 g, 0.082 ml, 0.866 mmol) was added with stirring to a suspension of thione 1 (0.3 g,
0.866 mmol) in glacial acetic acid (11 ml) and the mixture was boiled for 18 h. The crystals of compound 7
formed were filtered off and recrystallized.
N-[2-Acetyl-5-(4,6-diphenyl-2-pyrimidinyl)-3-thioxo-3,4-dihydro-2H-1,2,4-triazol-4-yl]diacetamide (8).
A mixture of thione 3 (0.2 g, 0.577 mmol) and freshly distilled acetic anhydride (2.16 g, 2.0 ml, 21.2 mmol) was
boiled with stirring for 1 h. After cooling the reaction mixture the precipitated crystals of product 8 were filtered off,
washed with ether, dried, and recrystallized.
N-5-(4,6-Diphenyl-2-pyrimidinyl)-3-thioxo-3,4-dihydro-2H-1,2,4-triazol-4-yl]diacetamide (9). Thione 1
(3 g, 0.866 mmol) was dissolved on heating in absolute pyridine (11 ml). Acetyl bromide (0.11 g, 0.065 ml,
0.866 mmol) was added dropwise to the cooled solution at room temperature and the mixture was boiled with stirring
for 1 h. The solution was cooled and the precipitate of pyridinium bromide was filtered off. The filtrate was poured
onto crushed ice and kept for one day. The precipitate of product 9 was filtered off, washed with water, dried, and
recrystallized.
N-[5-(4,6-Diphenyl-2-pyrimidinyl)-3-thioxo-3,4-dihydro-2H-1,2,4-triazol-4-yl]benzamide (10). A
mixture of thione 1 (0.3 g, 0.866 mmol), benzoic acid (0.11 g, 0.866 mmol), and freshly distilled phosphorus
oxychloride (1 ml) was boiled for 30 min. The reaction mixture was cooled, poured onto crushed ice, and
neutralized with potash. The solid residue of compound 10 was filtered of, washed with water, and
recrystallized.
6-Phenyl-3-(4,6-diphenyl-2-pyrimidinyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (11) was synthesized
analogously to compound 10, with the difference that the reaction mixture was boiled for 5 h. The cooled
solution was poured onto crushed ice. The precipitate of product 11 was filtered off, washed with 1.25% KOH
solution, water, methanol, and ether, dried, and recrystallized.
4-Ethoxymethylendenamino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-thione
(12). A suspension of thione 1 (0.25 g, 0.722 mmol) in ethyl orthoformate (2 ml) was boiled for 1 h. The reaction
mixture was cooled. Crystals of product 12 were filtered off, washed, and recrystallized.
924

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