Ultrasound irradiated synthesis of bis-pyrimidine derivative in aqueous media

Article abstract of DOI:10.1080/00397911.2011.558970

Pyrimidine derivatives have been found to possess a broad spectrum of biological activities. Among various pyrimidine derivatives, bis-pyrimidine seems to be the rarely studied. A variety of methods have been reported for the preparation of this class of

Full text of DOI:10.1080/00397911.2011.558970

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Ultrasound Irradiated Synthesis of Bis-
pyrimidine Derivative in Aqueous MediA
Vijay V. Dabholkar a & Faisal Y. Ansari a
a Department of Chemistry, Organic Research Laboratory , K.C.
College , Churchgate , Mumbai , India
Accepted author version posted online: 15 Dec 2011.Published
online: 14 May 2012.
To cite this article: Vijay V. Dabholkar & Faisal Y. Ansari (2012) Ultrasound Irradiated Synthesis
of Bis-pyrimidine Derivative in Aqueous MediA, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 42:16, 2423-2431, DOI:
10.1080/00397911.2011.558970
To link to this article: http://dx.doi.org/10.1080/00397911.2011.558970
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Synthetic Communications1, 42: 2423–2431, 2012
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2011.558970
ULTRASOUND IRRADIATED SYNTHESIS OF
BIS-PYRIMIDINE DERIVATIVE IN AQUEOUS MEDIA
Vijay V. Dabholkar and Faisal Y. Ansari
Department of Chemistry, Organic Research Laboratory, K.C. College,
Churchgate, Mumbai, India
GRAPHICAL ABSTRACT
Abstract Pyrimidine derivatives have been found to possess a broad spectrum of biological activi-
ties. Among various pyrimidine derivatives, bis-pyrimidine seems to be the rarely studied. A var-
iety of methods have been reported for the preparation of this class of compound. However, in
spite of their potential utility, some of the reported methods suffer from drawbacks such as long
reaction times, cumbersome product-isolation procedures, and environmental concerns. Organic
reactions in aqueous media have attracted increasing interest recently because of environmental
issues and the understanding of biochemical processes. Ultrasound has increasingly been used in
organic synthesis for greater yields, shorter reaction times or milder conditions.
Keywords Aqueous media; bis-pyrimidine; conventional method; sonication method
INTRODUCTION
Highly functionalized pyrimidine derivatives are of great importance to the
life-science industries, and many pyrimidine derivatives have been used for various
medicinal applications (Fig. 1).[1–3] Pyrimidine derivatives and heterocyclic annelated
Received December 3, 2010.
Address correspondence to Vijay V. Dabholkar, Department of Chemistry, Organic Research
Laboratory, K. C. College, Dinshaw Waccha Road, Churchgate, Mumbai 400 020, India. E-mail:
ansarifaisal_55@yahoo.co.in
2423

2424
V. V. DABHOLKAR AND F. Y. ANSARI
Figure 1. Pharmaceutical with subpyrimidine subunit.
pyrimidines continue to attract great interest because of the wide variety of interest-
ing biological activities observed for these compounds, such as anticancer,[4] anti-
viral,[5] antitumor,[6] anti-inflammatory,[7] and antimicrobial activities [8]. Among
various pyrimidine derivatives, bis- pyrimidines derivatives seem to be rarely studied.
A variety of methods have been reported for the preparation of this class of com-
[9]
pounds. In 2007, Nagaraj and Reddy
reported that the reaction of a, b unsatu-
rated carbonyl with carbamide, thiocarbamide, and guanidine hydrochloride in
the presence of potassium hydroxide was carried out in the absolute ethanol, but
it suffered disadvantages such as longer reaction time (5–8 h) and economic and
environmental concerns.
The recent interest in green chemistry has posed a new challenge for organic
synthesis in that new reaction conditions need to be found that reduce the emission
of volatile organic solvents and the use of hazardous toxic chemicals. Organic reac-
tions in aqueous media have attracted interest because of environmental issues and
the understanding of biochemical processes. As a reaction solvent, water offers many
practical and economic advantages including low cost, safe handling, and environ-
mental compatibility. Considering these facts many reactions using aqueous media
have been reported.[10–12]
Ultrasound increasingly has been used in organic synthesis in the past three
decades compared with traditional methods. When an ultrasonic wave propagates
through a liquid, the local pressure varies with time and space. If a bubble is present
in the liquid, its radius will expand and contract in response to these pressure
changes. For low-amplitude pressure excursions, these oscillations are sinusoidal
and may last for many acoustic cycles, a phenomenon called stable cavitation. Under
certain conditions, however, these oscillations may become unstable, leading to the
rapid collapse of a bubble during a single acoustic half-cycle. This phenomenon is
called transient cavitation. High temperatures and pressures are generated within
the bubble during its final stage of collapse that are thought to produce hydrogen
atoms and hydroxyl radicals in aqueous solutions. Some investigators feel that the
temperature is sufficient to generate free radicals, which are sometimes produced
for stable cavitation as well. The ultrasound irradiation technique is more con-
venient, gives better yields, and reduces reaction time.[13–25]
Continuing our investigations[26–29] of the application of ultrasound in organic
synthesis, we report a swift and practical green procedure for the synthesis of
bis-pyrimidine from bis-cinamate with carbamide=thiocarbamides=guanidine in
sodium acetate–acetic acid aqueous solution under ultrasounic irradiation Scheme 1.

BIS-PYRIMIDINE DERIVATIVE
2425
Scheme 1. Bis-pyrimidine derivative.
RESULTS AND DISCUSSION
The reaction of 3,3-dimethyl-1,5-dihydroxy-1,4-cyclohexadiene
1
with
acetic anhydride yielded bis-1,5-[acetoxy]-3,3-dimethyl-1,4-cyclohexadiene, which
was converted into bis-1,5-[substituted cinnamate]-3,3-dimethyl-1,4-cyclohexadiene
2 when stirred with substituted aromatic aldehydes in presence of 2 N sodium
hydroxide for 1 h. Formation of compound 2 was evidenced by the appearance of
1
a signal at 7.8 ppm (a,b-unsaturated carbonyl) in the H NMR spectra and in the
infrared (IR) spectral band due to carbonyl at 1634 cmꢀ1. In the 13C NMR spectra,
=
the signal 188.24 ppm was observed due to O C<in compound 2. The reaction
of carbamide with a,b-unsaturated compounds in conjugation with carbonyl
afforded
bis-1,5[10H,50H-dihydro-60-(4
substitutedpheny)-20-oxo-pyrimidin-40-
oxy]-3,3-dimethyl-1,4-cyclohexadiene 3. In 1H NMR spectra of compound 3, the sig-
nal at 8.30 was observed due to –NH-, and in the IR spectra the bands at 3100 (-N-
H-) and 1620 cmꢀ1 (-C O-) were also confirmed. In 13C NMR spectra, the signals at
=
=
=
144.04 ppm and 162.33 ppm were observed due to –C N- and C O respectively.
Similarly, the bis-1,5-[substituted cinnamate]-3,3-dimethyl-1,4-cyclohexadiene
2 on treatment with thiocarbamide underwent cyclization to afford bis-1,5[10H,
50H-dihydro-60-(4-substitutedpheny)-20-thioxo-pyrimidin-40-oxy]-3,3-dimethyl-1,4-
cyclohexadiene 4 (Scheme 1).
Compound 4 showed the result as compound 3 except for the thioxo group,
which was at 196.34 ppm in the 13C NMR spectra. Guanidine hydrochloride treated
with
2
yielded
bis-1,5[10H,50H-dihydro-60-(4-substitutedpheny)-20-thioxo-
pyrimidin-40-oxy]-3,3-dimethyl-1,4-cyclohexadiene 5. The IR spectrum of 5 showed
NH2 stretching bands at 3243–3300 cmꢀ1. In its H NMR spectrum, the chemical
1

2426
V. V. DABHOLKAR AND F. Y. ANSARI
Table 1. Physical and analytical data of compounds 2, 3, 4, and 5
Entry
R
Mp (ꢁC)
Yield (%) method A
Yield (%) method B
Molecular weight
2a
2b
2c
3a
3b
3c
4a
4b
4c
5a
5b
5c
H
OCH3
OH
200–2
215–17
198–99
242–45
261–63
231–33
187–89
197–99
176–78
168–71
177–79
157–59
82.10
84.23
83.84
82.71
83.49
85.75
82.43
84.10
83.86
84.23
82.32
82.98
72.23
73.46
72.39
74.32
73.09
73.21
76.89
72.98
73.32
74.56
73.23
75.78
400.21
460.23
432.89
480.51
540.56
512.51
512.64
572.6
H
OCH3
OH
H
OCH3
OH
544.64
478.54
538.59
510.54
H
OCH3
OH
=
shifts due to NH2 were observed at 2.69 ppm. Appearance of two peaks due to C N
at 143.71 and 147.37 ppm in 13C NMR confirmed the formation of 5. It was observed
that in the presence of sodium acetate in aqueous acetic acid the yield of pyrimidines
was increased. To verify the effect of ultrasound irradiation, in the absence of ultra-
sound, we performed the reaction of bis-substituted cinnamate with carbamide=
thiocarbamides=guanidine by refluxing for 3–4 h. The yield of pyrimidine was
73–79% (Table 1). While under ultrasound irradiation, the reaction completed within
45 min at room temperature with 82–86% yield. It was clear that the ultrasound
could accelerate the reaction to obtain bis-pyrimidines. The compounds obtained
by both the routes were identical, as they showed the same melting points and similar
spectral data.
EXPERIMENTAL
Melting points of all synthesized compounds were determined in open capillary
tubes on an electrothermal apparatus and are uncorrected. The purity of the com-
pounds was monitored by thin-layer chromatography (TLC) on silica-gel-coated alu-
minium plates (Merck) as adsorbent and ultraviolet light as visualizing agent. IR
spectra (potassium bromide in cmꢀ1) were recorded on a Perkin-Elmer spectrophot-
1
ometer in the range of 4000–400 cmꢀ1. H NMR spectra were recorded on a Varian
500-MHz NMR spectrophotometer using deuteriochloroform as solvent and tri-
methylsilane as an internal standard (chemical shifts in d ppm), and mass (ms) spectra
were taken on a Jeol sx-102=PA-6000 (EI) spectrometer. CHN estimations were
recorded on a Carlo Erba 1108 (CHN) elemental analyzer. The experiment under
ultrasound irradiation was carried out in a probe sonicator manufactured by Dakshin.
Bis-1,5-[substituted cinnamate]-3,3-dimethyl-1,4-cyclohexadiene
(2a–c)
Method A (ultrasound). A mixture of substituted aromatic aldehyde
(0.02 mol), 1 (2.45 ml, 0.01 mol), and NaOH (10 ml, 20% w=v) in 5 ml of ethanol
was stirred and exposed to ultrasound irradiation for 35 min. The reaction mixture

BIS-PYRIMIDINE DERIVATIVE
2427
was monitored by TLC. After completion of the reaction, the product was separated
out, washed with solvent ether, and recrystallized from ethanol.
Method B (conventional). A solution of substituted aromatic aldehydes
(0.02 mol), 1 (2.45 ml, 0.01 mol), and NaOH (10 ml, 20% w=v) in 5 ml of ethanol
was stirred for 2.5 h. The reaction was monitored by TLC. After completion of
the reaction, the contents were poured on crushed ice. The solid obtained was filtered
off, washed with water, and recrystallized from ethanol to get compounds 2a–c.
Bis-1,5-[cinnamate]-3,3-dimethyl-1,4-cyclohexadiene (2a). This com-
pound was obtained as white crystals, mp 200–202 ꢁC; IR (potassium bromide) n
1
max=cmꢀ1: 2912 (CH), 1745 C O), 1625 (C C); H NMR (deuteriochloroform):
d 0.96 (s, 6-H, 2 ꢂ CH3), 2.44 (s, 2-H, CH2), 4.69 (s, 2-H, CH), 7.82 (s, 4H, a, b-
unsaturated carbonyl), 6.98–8.02 (m, 10-H, aromatic protons); 13C NMR: 27.28
=
=
=
(CH3)2, 37.33 (CH2), 74.23 (tetrahedral carbon), 108.21-131.56 (C C & Ar-C),
=
188.42 (C O), MS: m=z 402 (mþ2). Anal. calcd. for C26H24O4: C, 78.21; H, 6.01.
Found: C, 77.87; H, 6.21.
Bis-1,5-[4’’-methoxy cinnamate]-3,3-dimethyl-1,4-cyclohexadiene (2b).
This compound was obtained as light green crystals, mp 215–217 ꢁC; IR (potassium
1
bromide) n max=cmꢀ1: 2980 (CH), 1752 (C O), 1620 (C C); H NMR (deuterio-
chloroform): d 1.07 (s, 6-H, 2 ꢂ CH3), 2.25 (s, 2-H, CH2), 3.73 (s, 6-H, OCH3),
4.75 (s, 2-H, CH), 7.89 (s, 4-H, a,b-unsaturated carbonyl), 6.88–7.89 (m, 8-H, aro-
matic proton); 13C NMR: 26.32 (CH3)2, 37.89 (CH2), 41.21 (OCH3), 74.45 (tetra-
=
=
hedral carbon), 111.32–132.43 (C C & Ar-C), 189.09 (C O); MS: m=z 462 (mþ2).
=
=
Anal. calcd. for C28H28O6: C, 73.04; H, 6.08. Found: C, 72.84; H, 6.24.
Bis-1,5-[4’’-hydroxy cinnamate]-3,3-dimethyl-1,4-cyclohexadiene (2c).
This compound was obtained as yellow crystals, mp 198–199 ꢁC; IR (potassium bro-
1
mide) n max=cmꢀ1: 3421 (OH), 3012 (CH), 1631 (C O), 1610 (C C); H NMR
(deuteriochloroform): d 0.98 (s, 6-H, 2 ꢂ CH3), 2.34 (s, 2-H, CH2), 4.56 (s, H,
OH), 4.67 (s, 2-H, CH), 7.76 (s, 4-H, a,b-unsaturated carbonyl), 6.95–7.79 (m,
8-H, aromatic proton). 13C NMR: 26.86 (CH3)2, 37.64 (CH2), 40.76 (OCH3),
=
=
=
=
74.32 (tetrahedral carbon), 113.41–131.83 (C C & Ar-C), 189.98 (C O); MS: m=z
432 (mþ2). Anal. calcd. for C28H26O6: C, 72.22; H, 5.67. Found: C, 72.14; H, 5.63.
Bis-1,5[1’H,5’H-dihydro-6’-(substitutedpheny)-2’-oxo-pyrimidin-
4’-oxy]-3,3-dimethyl-1,4-cyclohexadiene (3a–c),
Bis-1,5[1’H,5’H-dihydro-6’-(substitutedpheny)-2’-thioxo-pyrimidin-
4’-oxy]-3,3-dimethyl-1,4-cyclohexadiene (4a–c), and Bis-1,5[5’H-6’-
(substitutedpheny)-2’-amino-pyrimidin-4’-
oxy]-3,3-dimethyl-1,4-cyclohexadiene (5a–c)
Method A (ultrasound). A mixture of carbamide=thiocarbamide=guanidine
(1.2 g, 0.02 mol), 2 (2.45 ml, 0.01 mol), and (2.46 g, 0.03 mol) sodium acetate was dis-
solved in an aqueous acetic acid solution (6 mL, HAc=H2O ¼ 2=1,v=v) in a 50-mL
conical flask. The mixture was exposed to ultrasound for 45 min. Upon completion
of the reaction (monitored on TLC), the mixture was poured on crushed ice. The

2428
V. V. DABHOLKAR AND F. Y. ANSARI
product precipitated out was filtered, washed with water, and recrystallized from
ethanol.
Method B (conventional). A solution of carbamide (1.2 g, 0.02 mol), 2
(2.45 ml, 0.01 mol), and sodium acetate (2.46 g, 0.03 mol) was dissolved in aqueous
acetic acid solution (6 mL, HAc=H2O ¼ 2=1,v=v) and refluxed on a water bath for
4 h. The reaction was monitored by TLC. After completion of the reaction, the con-
tents were poured on crushed ice. The solid obtained was filtered off, washed with
water, and recrystallized from ethanol.
Bis-1,5[1’H,5’H-dihydro-6’-(pheny)-2’-oxo-pyrimidin-4’-oxy]-3,3-dimethyl-
1,4-cyclohexadiene (3a). This compound was obtained as brown crystals, mp
242–245 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3100 (NH), 2930 (CH), 1620
1
=
=
(C O), 1589 (C N), 1322 (C-N), H NMR (deuteriochloroform): d 0.97 (s, 6-H,
2 ꢂ CH3), 2.44 (s, 2-H, CH2), 4.72 (s, 2-H, CH), 7.12–7.45 (m, 12-H, C-H &
Ar-H), 8.30 (s, 2-H, NH); 13C NMR: 27.28 (2 ꢂ CH3), 32.18 (CH2), 73.54 (tetra-
=
=
=
hedral carbon), 115-128.33 (C C & Ar-C), 144.01 (C N), 162.32 (C O). MS:
m=z 482 (mþ2). Anal. calcd. for C28H24N4O4: C, 69.99; H, 5.03; N, 11.66. Found:
C, 69.95; H, 5.02, N, 11.61.
Bis-1,5[1’H,5’H-dihydro-6’-(4’-methoxypheny)-2’-oxo-pyrimidin-4’-oxy]-
3,3-dimethyl-1,4-cyclohexadiene (3b). This compound was obtained as yellow
crystals, mp 261–263 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3023 (NH), 2923
1
=
=
(CH), 1626 (C O), 1582 (C N), 1332 (C-N), H NMR (deuteriochloroform): d
0.96 (s, 6-H, 2 ꢂ CH3), 2.43 (s, 2-H, CH2), 3.91 (s, 6-H, OCH3), 4.56 (s, 2-H, CH),
7.03–7.56 (m, 10-H, C-H & Ar-H), 8.32 (s, 2-H, NH); 13C NMR: 27.23 (2 ꢂ CH3),
=
32.12 (CH2), 42.12 (OCH3), 73.21 (tetrahedral carbon), 112.23-128.33 (C C &
Ar-C), 144.23 (C N), 164.10 (C O). MS: m=z 542 (mþ2). Anal. calcd. for
C30H28N4O6: C, 69.66; H, 5.22; N, 10.36. Found: C, 69.62; H, 5.18, N, 11.32.
=
=
Bis-1,5[1’H,5’H-dihydro-6’-(4’-hydroxypheny)-2’-oxo-pyrimidin-4’-oxy]-
3,3-dimethyl-1,4-cyclohexadiene (3c). This compound was obtained as colorless
crystals, mp 231–233 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3320 (OH), 3009
1
=
=
(NH), 2910 (CH), 1614 (C O), 1576 (C N), 1339 (C-N); H NMR (deuteriochloro-
form): d 0.99 (s, 6-H, 2 ꢂ CH3), 2.47 (s, 2-H, CH2), 4.60 (s, 2-H, CH), 5.09 (s, 2-H,
OH), 6.98–7.43 (m, 10-H, C-H & Ar-H), 8.28 (s, 2-H, NH). 13C NMR: 28.01
=
(2 ꢂ CH3), 32.32 (CH2), 73.45 (tetrahedral carbon), 110.56–128.33 (C C & Ar-C),
145.10 (C N), 165.04 (C O); MS: m=z 514 (mþ2). Anal. calcd. for C28H24N4O6:
C, 65.62; H, 4.72; N, 10.93. Found: C, 65.59; H, 4.69, N, 10.89.
=
=
Bis-1,5[1’H,5’H-dihydro-6’-(pheny)-2’-thioxo-pyrimidin-4’-oxy]-3,3-dimethyl-
1,4-cyclohexadiene (4a). This compound was obtained as brown crystals, mp
187–189 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3043 (NH), 2924 (C-H), 1220
1
=
=
(C S), 1579 (C N), 1345 (C-N); H NMR (deuteriochloroform): d 0.96 (s, 6-H,
2 ꢂ CH3), 2.43 (s, 4-H, CH2), 4.74 (s, 2-H, CH), 7.11-7.63 (m, 12-H, C-H &
Ar-H), 8.27 (s, 2-H, NH). 13C NMR: 27.12 (2 ꢂ CH3), 31.79 (CH2), 73.89 (tetra-
=
=
=
hedral carbon), 115.23-131.47 (C C & Ar-C), 144.65 (C N), 196.34 (C S); MS:
m=z 514 (mþ2). Anal. calcd. for C28H24N4O2S2: C, 65.60; H, 4.72; N, 10.93; S,
12.51. Found: C, 65.58; H, 4.68, N, 10.89; S, 12.48.

BIS-PYRIMIDINE DERIVATIVE
2429
Bis-1,5[1’H,5’H-dihydro-6’-(4-methoxypheny)-2’-thioxo-pyrimidin-4’-
oxy]-3,3-dimethyl-1,4-cyclohexadiene (4b). This compound was obtained as
white crystals, mp 197–199 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3020 (NH),
1
=
=
2901 (C-H), 1224 (C S), 1556 (C N), 1331 (C-N), H NMR (deuteriochloroform):
d 0.95 (s, 6-H, 2 ꢂ CH3), 2.44 (s, 4-H, CH2), 3.89 (s, 6-H, OCH3), 4.71 (s, 2-H, CH),
7.00–7.87 (m, 10-H, C-H & Ar-H), 8.10 (s, H, NH). 13C NMR: 27.29 (2 ꢂ CH3),
=
32.41 (CH2), 42.23 (OCH3), 73.74 (tetrahedral carbon), 113.03–136.31 (C C &
Ar-C), 145.00 (C N), 195.67 (C S); MS: m=z 574 (mþ2). Anal. calcd. for
C30H28N4O4S2: C, 62.92; H, 4.93; N, 9.78; S, 11.20. Found: C, 62.89; H, 4.89, N,
9.76; S, 11.15.
=
=
Bis-1,5[1’H,5’H-dihydro-6’-(4-hydroxypheny)-2’-thioxo-pyrimidin-4’-oxy]-
3,3-dimethyl-1,4-cyclohexadiene (4c). This compound was obtained as light
yellow crystals, mp 176–178 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3412 (OH),
1
=
=
2990 (NH), 2982 (C-H), 1228 (C S), 1551 (C N); 1339 (C-N); H NMR (deuterio-
chloroform): d 0.98 (s, 6-H, 2 ꢂ CH3), 2.43 (s, 4-H, CH2), 4.72 (s, 2-H, CH), 5.65 (s,
2-H, OH), 7.17-7.67 (m, 10-H, C-H & Ar-H), 8.29 (s, 2-H, NH); 13C NMR: 28.21
=
(2 ꢂ CH3), 31.28 (CH2), 73.79 (tetrahedral carbon), 112.18–135.56 (C C & Ar-C),
144.23 (C N), 196.29 (C S). MS: m=z 546 (mþ2). Anal. calcd. for C28H24N4O4S2:
C, 61.75; H, 4.44; N, 10.29; S, 11.77. Found: C, 61.71; H, 4.40, N, 10.25; S, 11.72.
=
=
Bis-1,5[5’H-6’-(pheny)-2’-amino-pyrimidin-4’-oxy]-3,3-dimethyl-1,
4-cyclohexadiene (5a). This compound was obtained as green crystals, mp
168–171 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3243 (NH2), 2910 (C-H), 1567
1
=
(C N), 1378 (C-N); H NMR (deuteriochloroform): d 0.97 (s, 6-H, 2 ꢂ CH3), 2.44
(s, 2-H, CH2), 2.69 (s, 4-H, NH2), 4.75 (s, 2-H, CH), 7.03–7.73 (m, 12-H, C-H &
Ar-H); 13C NMR: 27.32 (2 ꢂ CH3), 32.43 (CH2), 74.09 (tetrahedral carbon),
112.58–135.23 (C C & Ar-C), 143.71 (C N), 147.37 (C N); MS: m=z 480 (mþ2).
Anal. calcd. for C28H26N6O2: C, 70.28; H, 5.48; N, 17.56. Found: C, 70.24; H,
5.42, N, 11.53.
=
=
=
Bis-1,5[5’H-6’-(4’-methoxypheny)-2’-amino-pyrimidin-4’-oxy]-3,3-dimethyl-
1,4-cyclohexadiene (5b). This compound was obtained as yellow crystals, mp
177–179 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3221 (NH2), 2978 (C-H), 1532
1
=
(C N), 1345 (C-N); H NMR (deuteriochloroform): d 0.99 (s, 6-H, 2 ꢂ CH3), 2.43
(s, 2-H, CH2), 2.64 (s, 4-H, NH2), 3.90 (s, 6-H, OCH3), 4.74 (s, 2-H, CH),
7.08–7.75 (m, 10-H, C-H & Ar-H); 13C NMR: 26.68 (2 ꢂ CH3), 31.23 (CH2), 74.89
=
=
(tetrahedral carbon), 112.12–134.156 (C C & Ar-C), 144.32 (C N), 146.56
=
(C N); MS: m=z 540 (mþ2). Anal. calcd. for C30H30N6O4: C, 66.90; H, 5.61; N,
15.60. Found: C, 66.87; H, 5.58, N, 15.58.
Bis-1,5[5’H-6’-(4’-hydroxypheny)-2’-amino-pyrimidin-4’-oxy]-3,3-dimethyl-
1,4-cyclohexadiene (5c). This compound was obtained as colorless crystals, mp
157–159 ꢁC; IR (potassium bromide) n max=cmꢀ1: 3412 (OH), 3235 (NH2), 2923
1
=
(C-H), 1543 (C N), 1339 (C-N); H NMR (deuteriochloroform): d 0.97 (s, 6-H,
2 ꢂ CH3), 2.44 (s, 2-H, CH2), 2.66 (s, 4-H, NH2), 4.76 (s, 2-H, CH), 5.03 (s, 2-H,
OH), 7.02–7.68 (m, 10-H, C-H & Ar-H); 13C NMR: 27.54 (2 ꢂ CH3), 32.87 (CH2),
=
73.34 (tetrahedral carbon), 112.45–133.23 (C C & Ar-C), 144.45 (C N), 146.5
=

2430
V. V. DABHOLKAR AND F. Y. ANSARI
(C N); MS: m=z 512 (mþ2). Anal. calcd. for C28H26N6O4: C, 65.87; H, 5.13; N,
16.46. Found: C, 65.85; H, 5.10, N, 16.42.
=
CONCLUSION
We have described a practical and convenient procedure for the synthesis of
bis-pyrimidine in sodium acetate–acetic acid aqueous solution at room temperature
under ultrasounic irradiation as well as conventional method.
ACKNOWLEDGMENTS
The authors are grateful to the principal, Manju J. Nichani, and management
of K. C. College, Mumbai, for providing the necessary facilities and to the head of
the Department of Microbiology for antimicrobial studies. The authors are also
thankful to the director, Institute of Science, Mumbai, for providing spectral
analyses.
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