Three component condensation reaction as an efficient route for the synthesis of furo[2,3-d]pyrimidines

Article abstract of DOI:10.2174/157017812799304079

The condensation reactions of alkyl isocyanides with 1,3-dimethylbarbituric acid and aryl carboxaldehydes to afford 6-(alkylamino)-5-(3-aryl)-1,3- dimethylfuro[2,3-d]pyrimidine-2,4(1H,3H)-dione, in excellent yields under neutral conditions, are reported.

Full text of DOI:10.2174/157017812799304079

Letters in Organic Chemistry, 2012, 9, 7-11
7
Three Component Condensation Reaction as an Efficient Route for the
Synthesis of Furo[2,3-d]pyrimidines
Ali Aminkhani*,a and Ghasem Marandi*,b
aDepartment of Chemistry, Islamic Azad University, Khoy Branch, Khoy, Iran
bShahid Bakeri High Education Center of Miandoab, Urmia University, Urmia, Iran
Received June 01, 2011: Revised October 02, 2011: Accepted November 11, 2011
Abstract: The condensation reactions of alkyl isocyanides with 1,3-dimethylbarbituric acid and aryl carboxaldehydes to
afford 6-(alkylamino)-5-(3-aryl)-1,3-dimethylfuro[2,3-d]pyrimidine-2,4(1H,3H)-dione, in excellent yields under neutral
conditions, are reported.
Keywords: Aldehydes, condensation reaction, fused heterocycles, isocyanides, 1,3-dimethylbarbituric acid, 1,3-
dimethylfuro[2,3-d]pyrimidine.
INTRODUCTION
supported by their IR and mass spectrometry as well as
elemental analyses (Scheme 1).
Some reagents such as isocyanides are useful reagents for
synthesis of organic structures [1, 2]. There are many diverse
cycloaddition reactions in which isocyanides play a key role
for synthesis of different types of heterocycles [3-7]. A
general feature of isocyanide reactions is the formation of
ꢀ,ꢀ-addition reaction products: i.e. two new bonds are
formed to the terminal isocyanide carbon atom. Typical
examples are the reaction of isocyanide with protonic acids,
carbon-oxygen and carbon-carbon double bond or triple
bond of electron-deficient compounds [2, 3, 8]. Fused
heterocyclic structures containing pyrimidine or furan rings
exhibited diverse biological activities such as antimicrobial
[9, 10], anti-inflammatory [11], antiviral [12], anti HIV [13]
and antitumor [14].
The 1H NMR spectrum of 4a exhibited three sharp
singlets ꢁ = 1.16, 3.37 and 3.55 ppm arising from both tert-
butyl and N-methyl groups, respectively. NH proton of 4a
appeared at ꢁ = 3.34 ppm as a broad signal which was
disappeared in D2O exchange experiment. All arylic protons
resonate at aromatic region (ꢁ = 7.22-7.61 ppm).
The 1H decoupled 13C NMR spectrum of 4a showed four
signals readily recognized as arising from two NCH3 group
(ꢁ = 27.25 and 28.38 ppm), three methyl of tert-butyl (ꢁ =
29.16 ppm) and quaternary carbon of tert-butyl group (ꢁ =
53.48 ppm) as well as other twelve distinct resonances in
agreement with the proposed structure. The characteristic
signals for the carbonyl groups of C-2 and C-4 were
observed at ꢁ 150.48 and 157.02 ppm, respectively.
In continuation of our investigations on development of
synthesis of five and six membered rings [6, 15-20], we now
describe the synthesis of furo[2,3-d]pyrimidine derivatives
containing a cyclohexyl or tert-butylamine substitution on C-
2 position of furan ring by means of a mild one-pot reaction
between aldehydes and isocyanides in the presence of 1,3-
dimethylbarbituric acid.
The IR spectrum of compound 4a at the carbonyl region
displayed distinct absorption bands resulting from the
carbonyl and NH groups respectively for each compound.
An illustrative mechanism for this reaction is shown in
Scheme 2. The first step may involve a Knovenagel
condensation between the aldehyde 2a and 1,3-
dimethylbarbituric acid 3 for the formation of the stable
intermediate enone 5, which undergoes nucleophilic attack
by isocyanide 1a to generate adduct 6. This adduct undergo
intra nucleophilic addition by oxanion for cyclization
process of five-member ring to afford compound 7 which
then can undergo tautomerization to output the final
compound 4a.
RESULTS AND DISCUSSION
Herein,
a
number of new furo[2,3-d]pyrimidine
derivatives 4 were prepared using isocyanides 1, aldeydes 2
and 1,3-dimethylbarbituric acid 3 at room temperature
reaching completion in 6-15 hours. The structural
assignments of the desired 5-aryl-6-(alkylamino)-1,3-
dimethylfuro[2,3-d]pyrimidine derivatives 4a-k were made
It must be mentioned that the effects of substitution
(electron donating or electron with drawing groups) on aryl
ring have been investigated in this reaction. Additional
experiments showed that the benzaldehydes with electron
donating substituents have not satisfactory results, whereas
benzaldehydes containing electron with drawing substituents
react with any side product formation. For example, no
reaction between p-N,N-dimethylaminobenzaldehyde or 2,4-
dimethoxy benzaldehyde and 1,3-dimethylbarbituric acid in
1
on the basis of their H and 13C NMR spectra which are
*Address correspondence to these authors at the Department of Chemistry,
Islamic Azad University, Khoy Branch, Khoy, Iran; Tel: +984612550001;
Fax: +984612550026; E-mail: ali_aminkhani@yahoo.com
Shahid Bakeri High Education Center of Miandoab, Urmia University,
Urmia, Iran; Tel: +984812265960; Fax: +984812245725;
E-mail: marandi_gh@yahoo.com
1875-6255/12 $58.00+.00
© 2012 Bentham Science Publishers

8
Letters in Organic Chemistry, 2012, Vol. 9, No. 1
Aminkhani and Marandi
O
H3C
O
CH3
O
N
N
O
H3C
O
CH3
O
CH2Cl2
r.t.
N
N
R
N
C
Ar CHO
+
+
Ar
1
N
R
2
3
4
H
a
Ar
4
R
time (h)
% yield
97
a
b
c
t-butyl
6
3-chlorophenyl
4-chlorophenyl
t-butyl
11
97
94
cyclohexyl
t-butyl
4-chlorophenyl
4-methylphenyl
4-methylphenyl
9
d
e
12
13
13
96
92
98
87
cyclohexyl
t-butyl
f
2-chlorophenyl
cyclohexyl
g
2-chlorophenyl
2-methylphenyl
2-methylphenyl
2,4-dichlorophenyl
10
t-butyl
h
i
15
9
94
cyclohexyl
96
86
11
8
j
t-butyl
2,4-dichlorophenyl
k
cyclohexyl
91
a All reaction times are reported base on TLC monitoring.
Scheme 1.
O
O
CHO
O
N
N
H
N
N
H
N
N
+
O
O
O
O
Cl
H
O
O
N
C
2a
3
1a
C
5
H
N
Cl
O
6
Cl
O
N
N
N
N
[1,3] H shift
O
O
N
O
O
N
Cl
Cl
H
H
7
4a
Scheme 2.
the presence of isocyanides for the synthesis of other
analogous of compound 4 was observed.
In conclusion, we have reported the in situ synthesis of 5-
aryl-6-(alkylamino)-1,3-dimethylfuro[2,3-d]pyrimidine

Three Component Condensation Reaction
Letters in Organic Chemistry, 2012, Vol. 9, No. 1
9
derivatives by an efficient and simple approach along with
three-component condensation between aromatic aldehydes,
1,3-dimethylbarbituric acid and isocyanides.
Hz, 2 CHarom), 7.55 (2H, d, J = 8.4 Hz, 2 CHarom). 13C NMR
(100.1 MHz, CDCl3): 27.21 and 28.70 (2s, 2 NCH3), 29.16
(s, NCMe3), 53.51 (s, NCMe3), 94.41 (s, C-4a), 109.70 (s, C-
5), 127.24 (s, 2 CHarom), 127.96 (s, Carom), 129.89 (s, 2
CHarom), 132.15 (s, Carom), 146.97 (s, C-6), 149.45 (s, C-7a),
150.60 (s, C-2), 157.14 (s, C-4).
EXPERIMENTAL
Melting points and IR spectra of all compounds were
measured on an Electrothermal 9100 apparatus and a
Shimadzu Prestige 21 FT-IR spectrometer, respectively.
6-(Cyclohexylamino)-5-(4-chlorophenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4c)
°
1
Also, the H and 13C NMR spectra were obtained with a
White powder, yield: 0.36 g (94%), mp 151-154 C, IR
(KBr) (vmax, cm-1): 3311 (NH), 1701 and 1693 (C=O). MS
(m/z, %): 389 (M++2, 5), 388 (M++1, 3), 387 (M+, 13), 305
(10), 293 (100), 279 (3),139 (38), 126 (6), 111 (27), 99 (5),
75 (17), 58 (25), 41 (16).Anal. Calcd. for C20H22ClN3O3
(387.86): C, 61.93; H, 5.72; N, 10.83%. Found: C, 61.99; H,
BRUKER DRX-400 AVANCE instruments using CDCl3 as
a solvent and TMS as internal standard at (400.1, 100.1)
MHz, respectively. Elemental analyses for C, H and N were
performed using a Heraeus CHN-O-Rapid analyzer. In
addition, the mass spectra were recorded on a Shimadzu
GCMS-QP5050A mass spectrometer operating at an
ionization potential of 70 eV. Isocyanides, 1,3-
dimethylbarbituric acid and aromatic carbaldehyde
derivatives were purchased from Fluka, Merck and Acros
companies and used without further purification.
1
5.67; N, 10.72%. H NMR (400.1 MHz, CDCl3): 1.11-1.92
(10H, m, 5 CH2 of cyclohexyl), 3.11-3.18 (1H, m, NCH),
3
3.37 (3H, s, NCH3), 3.48 (1H, d, JHH = 6.7 Hz, NH), 3.57
(3H, s, NCH3), 7.36 (2H, d, 3JHH = 8.5 Hz, 2 CHarom), 7.52
(2H, d, 3JHH = 8.5 Hz, 2 CHarom). 13C NMR (100.1 MHz,
CDCl3): 23.70 and 24.50 (2s, 3 CH2 of cyclohexyl), 27.25
and 28.72 (2s, 2 NCH3), 32.91 (s, CH2 of cyclohexyl), 54.51
(s, NCH), 94.80 (s, C-4a), 103.19 (s, C-5), 127.40 and
129.54 (2s, 4 CHarom), 131.80 and 135.10 (2s, 2 Carom),
147.75 (s, C-6), 149.35 (s, C-7a), 149.86 (s, C-2), 157.14 (s,
C-4).
General Procedure for Preparation of furo[2,3-
d]pyrimidine Derivatives (Exemplified by 4a)
To
a
magnetically
stirred
solution
of
3-
chlorocarbaldehyde 2 (1 mmol) and 1,3-dimethylbarbituric
acid 3 (1 mmol) in CH2Cl2 (10 mL) was added, dropwise, a
mixture of tert-butylisocyanide (1.1 mmol) in CH2Cl2 (3 mL)
over 10 min at room temperature. After 6 hours stirring at
room temperature, the solvent was removed and the crude
product washed by diethyl ether (2ꢀ3 mL), then the residual
was recrystalized in a mixture of ethyl acetate/n-hexane (3:1)
to afford final product 4a.
6-(tert-butylamino)-5-(4-methylphenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4d)
°
Pale white powder, yield: 0.33 g (96%), mp 162-165 C,
IR (KBr) (vmax, cm-1): 3284 (NH), 1705 and 1670 (C=O). MS
(m/z, %): 342 (M++1, 4), 341 (M+, 17), 326 (1), 285 (60),
293 (5), 259 (20), 156 (13), 57 (100), 41 (65). Anal. Calcd.
for C19H23N3O3 (341.40): C, 66.84; H, 6.79; N, 12.31%.
Found: C, 66.91; H, 6.87; N, 12.26%. 1H NMR (400.1 MHz,
CDCl3): 1.16 (9H, s, NCMe3), 2.36 (3H, s, ArCH3), 3.38
(3H, s, NCH3), 3.43 (1H, br s, NH), 3.55 (3H, s, NCH3), 7.21
(2H, d, J = 8.0 Hz, 2 CHarom), 7.44 (2H, d, J = 8.0 Hz,
CHarom). 13C NMR (100.1 MHz, CDCl3): 20.27 (s, ArCH3),
27.18 and 28.33 (2s, 2 NCH3), 29.18 (s, NCMe3), 53.31 (s,
NCMe3), 94.24 (s, C-4a), 110.06 (s, C-5), 126.39 (s, Carom),
127.43 and 128.35 (2s, 4 CHarom), 136.07 (s, Carom), 146.94
(s, C-6), 150.35 (s, C-7a), 149.88 (s, C-2), 157.14 (s, C-4).
6-(tert-butylamino)-5-(3-chlorophenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4a)
°
White powder, yield: 0.35 g (97%), mp 149-152 C, IR
(KBr) (vmax, cm-1): 3297 (NH), 1705 and 1689 (C=O). MS
(m/z, %): 363 (M++2, 15), 362 (M++1, 11), 361 (M+, 45), 346
(4), 305 (100), 293 (5), 250 (21), 248 (62), 75 (4), 57 (31).
Anal. Calcd. for C18H20ClN3O3 (361.82): C, 59.75; H, 5.57;
1
N, 11.61%. Found: C, 59.70; H, 5.68; N, 11.49%. H NMR
(400.1 MHz, CDCl3): 1.16 (9H, s, NCMe3), 3.34 (1H, br s,
NH), 3.37 and 3.55 (6H, 2s, 2 NCH3), 7.22-7.28 (1H, m,
CHarom), 7.32 (1H, t, J = 8.0 Hz, CHarom), 7.50 (1H, dt, J1 =
7.7, J2 = 1.2 Hz, CHarom), 7.61 (1H, t, J = 1.9 Hz, CHarom).
13C NMR (100.1 MHz, CDCl3): 27.25 and 28.38 (2s, 2
NCH3), 29.16 (s, NCMe3), 53.48 (s, NCMe3), 94.32 (s, C-
4a), 109.01 (s, C-5), 126.28, 126.84, 128.23 and 128.30 (4s,
4 CHarom), 131.27 and 132.73 (2s, 2 Carom), 147.20 (s, C-6),
149.38 (s, C-7a), 150.48 (s, C-2), 157.02 (s, C-4).
6-(Cyclohexylamino)-5-(4-methylphenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4e)
White powder, yield: 0.34 g (92%), mp 241-244 °C
(decomposed), IR (KBr) (vmax, cm-1): 3255 (NH), 1698 and
1691 (C=O). MS (m/z, %): 367 (M+, 1), 285 (2), 273 (100),
178 (9), 119 (65), 91 (63), 56 (93), 43 (53). Anal. Calcd. for
C21H25N3O3 (367.44): C, 68.64; H, 6.86; N, 11.44%. Found:
C, 68.72; H, 6.90; N, 11.53%. 1H NMR (400.1 MHz,
CDCl3): 0.88-2.17 (10H, m, 5 CH2 of cyclohexyl), 2.39 (3H,
s, ArCH3), 3.25 and 3.36 (6H, 2s, 2 NCH3), 3.85-3.93 (1H,
m, NCH), 5.20 (1H, d, 3JHH = 8.1 Hz, NH), 7.22 (2H, d, 3JHH
= 8.0 Hz, 2 CHarom), 7.35 (2H, d, 3JHH = 8.0 Hz, 2 CHarom).
13C NMR (100.1 MHz, CDCl3): 20.64 (s, ArCH3), 23.78 and
24.45 (2s, 4 CH2 of cyclohexyl), 27.74 and 27.80 (2s, 2
NCH3), 31.67 (s, CH2 of cyclohexyl), 47.78 (s, NCH), 94.77
(s, C-4a), 107.41 (s, C-5), 127.11 and 127.93 (2s, 4 CHarom),
130.39 and 131.79 (2s, 2 Carom), 140.44 (s, C-6), 150.11 (s,
C-7a), 150.75 (s, C-2), 160.03 (s, C-4).
6-(tert-butylamino)-5-(4-chlorophenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4b)
White powder, yield: 0.35 g (97%), mp 165-168 °C
(decomposed), IR (KBr) (vmax, cm-1): 3305 (NH), 1706 and
1698 (C=O). MS (m/z, %): 363 (M++2, 1), 361 (M+, 3), 341
(96), 326 (2), 285 (100), 257 (62), 156 (34), 57 (32), 41 (26).
Anal. Calcd. for C18H20ClN3O3 (361.82): C, 59.75; H, 5.57;
1
N, 11.61%. Found: C, 59.67; H, 5.64; N, 11.53%. H NMR
(400.1 MHz, CDCl3): 1.15 (9H, s, NCMe3), 3.31 (1H, br s,
NH), 3.37 and 3.55 (6H, 2s, 2 NCH3), 7.35 (2H, d, J = 8.4

10 Letters in Organic Chemistry, 2012, Vol. 9, No. 1
Aminkhani and Marandi
6-(tert-butylamino)-5-(2-chlorophenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4f)
C, 68.90; H, 6.81; N, 11.37%. 1H NMR (400.1 MHz,
CDCl3): 1.10-2.01 (10H, m, 5 CH2 of cyclohexyl), 2.33 (3H,
s, ArCH3), 3.22 and 3.38 (6H, 2s, 2 NCH3), 3.79-3.89 (1H,
°
Pale white powder, yield: 0.35 g (98%), mp 156-159 C,
IR (KBr) (vmax, cm-1): 3264 (NH), 1701 and 1670 (C=O). MS
(m/z, %): 363 (M++2, 14), 361 (M+, 40), 326 (1), 305 (100),
293 (7), 248 (65), 176 (76), 57 (49), 41 (29). Anal. Calcd. for
C18H20ClN3O3 (361.82): C, 59.75; H, 5.57; N, 11.61%.
Found: C, 59.63; H, 5.62; N, 11.58%. 1H NMR (400.1 MHz,
CDCl3): 1.17 (9H, s, NCMe3), 3.35 (1H, s, NH), 3.37 and
3.55 (6H, 2s, 2 NCH3), 7.25-7.28 (1H, m, CHarom), 7.32 (1H,
t, J = 7.9 Hz, CHarom), 7.51 (1H, dt, J1 = 7.6, J2 = 1.4 Hz,
CHarom), 7.62 (1H, t, J = 1.8 Hz, CHarom). 13C NMR (100.1
MHz, CDCl3): 27.26 and 28.38 (2s, 2 NCH3), 29.20 (s,
NCMe3), 53.50 (s, NCMe3), 94.38 (s, C-4a), 109.14 (s, C-5),
126.34, 126.89, 128.26 and 128.37 (4s, 4 CHarom), 131.44
and 132.81 (2s, 2 Carom), 147.24 (s, C-6), 149.45 (s, C-7a),
150.54 (s, C-2), 157.05 (s, C-4).
3
m, NCH), 5.23 (1H, d, JHH = 8.1 Hz, NH), 7.13 (H, d, J =
7.5 Hz, CHarom), 7.16-7.31 (3H, m, 3 CHarom). 13C NMR
(100.1 MHz, CDCl3): 18.97 (s, ArCH3), 23.71 and 24.45 (2s,
3 CH2 of cyclohexyl), 27.67 and 27.81 (2s, 2 NCH3), 31.60
and 31.62 (2s, 2 CH2 of cyclohexyl), 47.65 (s, NCH), 94.18
(s, C-4a), 117.03 (s, C-5), 123.59, 124.92, 127.91 and 129.24
(4s, 4 CHarom), 133.27 and 134.76 (2s, 2 Carom), 142.13 (s, C-
6), 149.73 (s, C-7a), 158.63 (s, C-2), 159.21 (s, C-4).
6-(tert-butylamino)-5-(2,4-dichlorophenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4j)
°
Pale white powder, yield: 0.34 g (86%), mp 174-177 C
(decomposed), IR (KBr) (vmax, cm-1): 3286 (NH), 1703 and
1685 (C=O). MS (m/z, %): 400 (M++4, 1), 398 (M++2, 4),
396 (M+, 7), 339 (5), 305 (3), 293 (100), 277 (11), 173 (13),
57 (43), 41 (17). Anal. Calcd. for C18H19Cl2N3O3 (396.27):
C, 54.56; H, 4.83; N, 10.60%. Found: C, 54.59; H, 4.80; N,
10.67%. 1H NMR (400.1 MHz, CDCl3): 1.37 (9H, s,
NCMe3), 3.24 and 3.38 (6H, 2s, 2 NCH3), 3.45 (1H, br s,
NH), 7.29-7.34 (2H, m, CHarom), 7.46 (1H, d, J = 1.8 Hz,
CHarom). 13C NMR (100.1 MHz, CDCl3): 27.62 and 28.65
(2s, 2 NCH3), 27.87 (s, NCMe3), 56.53 (s, NCMe3), 94.52 (s,
C-4a), 107.58 (s, C-5), 126.54, 126.89 and 128.21 (3s, 3
CHarom), 129.77, 131.35 and 134.11 (3s, 3 Carom), 147.36 (s,
C-6), 148.67 (s, C-7a), 151.02 (s, C-2), 156.94 (s, C-4).
6-(Cyclohexylamino)-5-(2-chlorophenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4g)
White powder, yield: 0.34 g (87%), mp 170-173 °C
(decomposed), IR (KBr) (vmax, cm-1): 3267 (NH), 1701 and
1694 (C=O). MS (m/z, %): 389 (M++2, 39), 388 (M++1, 34),
387 (M+, 100), 352 (2), 305 (54), 277 (96), 248 (31), 101
(10), 83 (33), 67 (85), 41 (42). Anal. Calcd. for
C20H22ClN3O3 (387.86): C, 61.93; H, 5.72; N, 10.83%.
Found: C, 62.01; H, 5.68; N, 10.89%. 1H NMR (400.1 MHz,
CDCl3): 1.11-2.02 (10H, m, 5 CH2 of cyclohexyl), 3.39 and
3.56 (6H, 2s, 2 NCH3), 3.62-3.68 (1H, m, NCH), 6.21 (1H,
6-(Cyclohexylamino)-5-(2,4-dichlorophenyl)-1,3-dimethyl-
furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (4k)
3
d, JHH = 8.6 Hz, NH), 7.28-7.35 (2H, m, 2 CHarom), 7.47
(1H, dt, J1 = 7.8, J2 = 1.3 Hz, CHarom), 7.58 (1H, t, J = 1.6
Hz, CHarom). 13C NMR (100.1 MHz, CDCl3): 23.73 (s, CH2
of cyclohexyl), 27.31 and 28.44 (2s, 2 NCH3), 31.58 and
32.95 (2s, 4 CH2 of cyclohexyl), 54.46 (s, NCH), 93.81 (s,
C-4a), 106.32 (s, C-5), 125.84, 126.53, 128.02 and 129.08
(4s, 4 CHarom), 131.37 and 133.10 (2s, 2 Carom), 148.04 (s, C-
6), 149.13 (s, C-7a), 150.07 (s, C-2), 157.43 (s, C-4).
°
Pale White powder, yield: 0.38 g (91%), mp 178-181 C,
IR (KBr) (vmax, cm-1): 3271 (NH), 1708 and 1693 (C=O). MS
(m/z, %): 426 (M++4, 1), 424 (M++2, 3), 423 (M++1, 9), 422
(M+, 4), 388 (2), 339 (6), 324 (3), 293 (100), 277 (42), 173
(38), 83 (58), 41 (32). Anal. Calcd. for C20H21Cl2N3O3
(422.30): C, 56.88; H, 5.01; N, 9.95%. Found: C, 56.92; H,
1
5.07; N, 9.87%. H NMR (400.1 MHz, CDCl3): 1.06-2.00
6-(tert-butylamino)-5-(2-methylphenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4h)
(10H, m, 5 CH2 of cyclohexyl), 3.11-3.14 (1H, m, NCH),
3.38 (1H, d, JHH = 5.2 Hz, NH), 3.41 and 3.56 (6H, 2s, 2
3
NCH3), 7.29-7.32 (2H, m, 2 CHarom), 7.47 (1H, d, 3JHH = 1.8
Hz, CHarom). 13C NMR (100.1 MHz, CDCl3): 23.63 and
24.47 (2s, 3 CH2 of cyclohexyl), 27.12 and 28.42 (2s, 2
NCH3), 32.85 (s, 2 CH2 of cyclohexyl), 54.06 (s, NCH),
95.72 (s, C-4a), 108.71 (s, C-5), 125.97 (s, CHarom), 126.91
(s, CHarom), 128.42 and 132.29 (2s, 2 Carom), 133.29 and
133.70 (2s, 2 Carom), 147.97 (s, C-6), 149.40 (s, C-7a),
149.94 (s, C-2), 156.80 (s, C-4).
°
Pale White powder, yield: 0.32 g (94%), mp 257-260 C
(decomposed), IR (KBr) (vmax, cm-1): 3284 (NH), 1700 and
1678 (C=O). MS (m/z, %): 342 (M++1, 9), 341 (M+, 38), 326
(2), 285 (100), 293 (5), 250 (21), 228 (43), 91 (22), 57 (71),
41 (37). Anal. Calcd. for C19H23N3O3 (341.40): C, 66.84; H,
1
6.79; N, 12.31%. Found: C, 66.78; H, 6.75; N, 12.26%. H
NMR (400.1 MHz, CDCl3): 1.37 (9H, s, NCMe3), 2.31 (3H,
s, ArCH3), 3.22 and 3.38 (6H, 2s, 2 NCH3), 5.16 (1H, br s,
NH), 7.12 (1H, d, J = 7.4 Hz, CHarom), 7.19-7.32 (3H, m, 3
CHarom). 13C NMR (100.1 MHz, CDCl3): 27.67 and 27.81
(2s, 2 NCH3), 29.04 (s, NCMe3), 52.55 (s, NCMe3), 94.27 (s,
C-4a), 108.65 (s, C-5), 123.47, 124.88, 128.23 and 129.25
(4s, 4 CHarom), 133.29 and 134.94 (2s, 2 Carom), 147.16 (s, C-
6), 149.73 (s, C-7a), 150.01 (s, C-2), 156.96 (s, C-4).
ACKNOWLEDGEMENT
Authors gratefully acknowledge financial support from
the Research Council of Khoy Branch Islamic Azad
University.
6-(Cyclohexylamino)-5-(2-methylphenyl)-1,3-dimethylfuro
[2,3-d]pyrimidine-2,4(1H,3H)-dione (4i)
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