Novel and efficient synthesis of pyrimidine derivatives

Article abstract of DOI:10.1080/00397910903108521

A new series of 1-alkyl-2-oxo-1,2-dihydro-pyrimidine-5-carboxalic acid amides is described. The reaction of N-((E)-3-(dimethylamino)-2-formylacryloyl) formamidine, an intermediate obtained by Vilsmeier-Haack formylation of acetonitrile with various mono-substituted ureas, provides such compounds in good yields. Copyright

Full text of DOI:10.1080/00397910903108521

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Novel and Efficient Synthesis of
Pyrimidine Derivatives
Maruti G. Ghagare a , Dilip R. Birari a , Deepak P. Shelar a ,
Raghunath B. Toche a & Madhukar N. Jachak a
a Organic Chemistry Research Centre, Department of Chemistry ,
KTHM College , Nashik, India
Published online: 06 May 2010.
To cite this article: Maruti G. Ghagare , Dilip R. Birari , Deepak P. Shelar , Raghunath B. Toche
& Madhukar N. Jachak (2010) Novel and Efficient Synthesis of Pyrimidine Derivatives, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry,
40:11, 1580-1587, DOI: 10.1080/00397910903108521
To link to this article: http://dx.doi.org/10.1080/00397910903108521
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Synthetic Communications1, 40: 1580–1587, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910903108521
NOVEL AND EFFICIENT SYNTHESIS OF PYRIMIDINE
DERIVATIVES
Maruti G. Ghagare, Dilip R. Birari, Deepak P. Shelar,
Raghunath B. Toche, and Madhukar N. Jachak
Organic Chemistry Research Centre, Department of Chemistry, KTHM
College, Nashik, India
A new series of 1-alkyl-2-oxo-1,2-dihydro-pyrimidine-5-carboxalic acid amides is described.
The reaction of N-((E)-3-(dimethylamino)-2-formylacryloyl) formamidine, an intermedi-
ate obtained by Vilsmeier–Haack formylation of acetonitrile with various mono-substituted
ureas, provides such compounds in good yields.
Keywords: Monosubstituted ureas; nucleophilic vinylic substitution; pyrimidine derivatives; synthesis
The reported methods for pyrimidine involves reaction of a 1,3-dicarbonyl compo-
nent with a reagent bearing an N-C-N fragment such as urea,[1] amidine,[2] or guani-
dine.[3] The use of formamide or an orthoester in combination with ammonia[4] as a
potential surrogate N-C-N reagent in the synthesis of pyrimidines has also been
reported. A variety of b-dicarbonyl compounds,[5] tris-(formylamino)methanes,[6] and
3-methyl-5-nitro-3H-pyrimidin-4-ones[7] have been used as synthons for 1,3-dicarbonyl
compounds in the synthesis.
In connection with our previous work,[8–10] we decided to study the reaction of
substituted ureas with 2 as an attractive procedure for pyrimidines. In the synthesis
of compounds 4a–e (Scheme 1, Table 1), the first step of the reaction always proceeds
via nucleophilic vinylic substitution (SNV) of the activated dimethylamino methylene
derivative. We first allowed 2 to react with 1.0 equiv of urea=N-substituted ureas 3a–e
in acidic medium at 50–60 ꢀC for 4–5 h, and we were pleased to find that such reac-
tion conditions afforded open chain compounds 4a–e in 78–83% yield. During this
condensation, it was observed that the N-formyl group in 2 undergoes hydrolysis
to amido function to yield 4a–e.
1
The H NMR spectrum of 4a revealed it to be 2-formyl-3-ureido-acrylamide.
In the 1H NMR spectrum of 4a, the aldehyde proton resonated at d 9.35, a doublet
resonated at d 11.46 corresponding to NH proton near to olefinic CH, and another
doublet resonated at d 8.20, representing the olefinic proton. The two NH2 groups
Received January 18, 2009.
Address correspondence to Madhukar N. Jachak, Organic Chemistry Research Centre,
Department of Chemistry, KTHM College, Gangapur Road, Nashik 422001, M.S., India. E-mail:
mn_jachak@hotmail.com
1580

NOVEL AND EFFICIENT SYNTHESIS OF PYRIMIDINE DERIVATIVES
1581
Scheme 1. Reaction of compound 2 with substituted ureas.
appeared as four broad singlets at d 8.15, 7.77, 7.52, and 7.28. In the 13C NMR
spectrum, a peak at d 191.5 corresponding to aldehyde carbon was observed. Peaks
at d 167.0 and 157.8 represent two amide carbonyl carbons. The olefinic carbon reso-
nated at d 152.1, and the remaining carbon appeared at d 107.8. The mass spectrum
of 4 displayed the molecular ion (Mþ) peak at 157 m=z, which is consistent with the
molecular weight of 4a. The structures of the other products 4b–e were established
on the basis of spectral analysis. (see Experimental data.)
In our attempts to cyclize 4a–e, we discovered that treatment of a mixture of
4a–e and triethylamine in acetonitrile at 60–70 ꢀC produced 5a–e in only 45–52%
yield. Because the yields of the resulting pyrimidines 5a–e were very low (Table 2),
we decided to substitute triethyl amine with t-BuOk in methanol as an alternate base.
Under these reaction conditions, 4a–e were cyclized to substituted pyrimidines 5a–e
in 89–95% yield. No further improvements in yields were seen by changing other
reaction conditions for the cyclization. The 1H NMR spectrum of 5a showed a sing-
let at d 8.66 representing two olefinic protons, a broad singlet at d 12.32 correspond-
ing to ring NH proton, and the two broad singlets at d 7.80 and 7.36 for the amide
protons of NH2. The 13C NMR spectrum of 5a showed five distinct signals in
agreement with the proposed structure. The mass spectrum of 5a displayed the
molecular ion (Mþ) peak at 139 m=z, which is consistent with the molecular weight
of 5a. All pyrimidine derivatives 5a–e were characterized by spectral analysis.
(see Experimental data.)
Alternatively, compounds 5b, c, and e were prepared from 5a by alkylation
using dimethylformamide (DMF)=K2CO3 at room temperature (Scheme 2).
Table 1. Synthesis of 4a–e and 5a–e
3, 4, 5
R
a
b
c
d
e
-H
-C2H5
-CH2C6H5
-C6H5
-CH2CH2C6H5

1582
M. G. GHAGARE ET AL.
Table 2. Yield optimization of pyrimidine derivatives
5
R
TEA=CH3CN (%)
t-BuOk=MeOH (%)
a
b
c
d
e
-H
-C2H5
45
47
52
50
47
89
92
95
90
93
-CH2C6H5
-C6H5
-CH2CH2C6H5
Scheme 2. Synthesis of 5b, c, e and 8a–d.
However, attempts for arylation of 5a with bromobenzene under similar reaction
conditions were unsuccessful. Compound 5a was further studied for N-alkylation
reactions with substituted anilides 7a–d. Thus, the condensation of 2-oxo-1,2-
dihydro-pyrimidine-5-carboxalic acid amide 5a with 1 equiv of anilide derivatives
7a–d in DMF using K2CO3 proceeded smoothly at room temperature to obtain the
corresponding N-substituted pyrimidines 8a–d in 87–91% yield (Scheme 2, Table 3).
In conclusion, we have established a simple and scalable synthesis of pyrim-
idine derivatives using N-((E)-3-(dimethylamino)-2-formylacryloyl) formamidine as
a convenient precursor. The simplicity and excellent yields make this method one
of the most attractive approaches to the pyrimidine synthesis.
EXPERIMENTAL
Melting points were determined on a Buchi melting-point apparatus, model
1
B-545, and are uncorrected. The H (300 MHz) and 13C (75 MHz) NMR spectra
were recorded on a Varian XL-300 spectrometer. Chemical shifts are reported in
Table 3. Synthesis of compounds 8a–d
7, 8
Ar
a
b
c
2,4-di-ClC6H3
4-Cl-3-F3CC6H3
4-ClC6H4
d
4-FC6H4

NOVEL AND EFFICIENT SYNTHESIS OF PYRIMIDINE DERIVATIVES
1583
parts per million (ppm) relative to tetramethylsilane (TMS), and multiplicities are
given as s (singlet), d (doublet), t (triplet), q (quartet), or m (multiplet). The solvent
for NMR spectra was dimethylsulfoxide (DMSO-d6) unless otherwise stated. Infra-
red (IR) spectra were taken on Thermo Electron Corporation Nicolet 380 Fourier
transform (FT)–IR instrument in potassium bromide pellets unless otherwise stated.
Mass spectrum was recorded on a Shimadzu GC-MS QP 2010A mass spectrometer
with an ionization potential of 70 eV. Elemental analyses were performed on a Hosli
CH-Analyzer and are within ꢁ0.4 of the theoretical percentage. All reactions were
monitored by thin-layer chromatography (TLC), carried out on 0.2-mm silica gel
60 F-254 (Merck) plates using ultraviolet (UV) light (254 and 366 nm) for detection.
Common reagent-grade chemicals are either commercially available (and were used
without further purification) or prepared by standard literature procedures.
General Procedure for the Synthesis of 4a–e
Concentrated hydrochloric acid (1.7 ml) was added to an equimolar solution of
2 (1.7 g, 10 mmol) and urea (0.6 g, 10 mmol) or N-substituted urea in ethanol (25 ml),
and the mixture was heated to 50–60 ꢀC for 4–5 h (TLC monitoring). After cooling,
the precipitate was collected by filtration and recrystallized from ethanol to afford
1.25 g of 4a as a yellow solid.
Selected Data
2-Formyl-3-ureido-acrylamide (4a). Yield: 80%; mp 194–197 ꢀC; IR (KBr):
1
3365, 3164, 1728, 1670, 1574, 1446, 1419, 1322, 1259, 1210, 1023 cmꢂ1; H NMR
(300 MHz, DMSO): d ¼ 11.46 (d, J ¼ 12 Hz,1H, -NH), 9.35 (s, 1H, -CHO), 8.20
(d, J ¼ 12 Hz, 1H, -CH), 8.15 (bs, 1H, -NH), 7.77 (bs, 1H, -NH), 7.52 (bs, 1H,
-NH), 7.28 (bs, 1H, -NH); 13C NMR (75 MHz, DMSO): d ¼ 191.5, 167.0, 157.8,
152.1, 107.8; MS (ESI): m=z ¼ 157 [M þ H]. Anal. calcd. for C5H7N3O3: C, 38.22;
H, 4.49; N, 26.75%. Found: C, 38.05; H, 4.20; N, 26.49%.
3-(3-Ethyl-ureido)-2-formyl-acrylamide (4b). White solid; 1.57 g, yield:
85%; mp 218–220 ꢀC; IR (KBr): 3381, 3254, 3064, 2969, 1723, 1548, 1452, 1392,
1
1345, 1316, 1234, 1103 cmꢂ1; H NMR (300 MHz, DMSO): d ¼ 11.61 (d, J ¼ 12 Hz,
1H, -NH), 9.23 (s, 1H, -CHO), 8.38 (t, J ¼ 5.1 Hz, 1H, -NH), 8.24 (d, J ¼ 12 Hz, 1H,
-CH), 8.18 (bs, 1H, -NH), 7.54 (bs, 1H, -NH), 3.21 (m, 2H, -CH2), 2.51(t,
J ¼ 1.65 Hz, 3H, -CH3); 13C NMR (75 MHz, DMSO): d ¼ 191.4, 167.2, 157.6,
151.3, 107.6, 34.6, 14.6; MS (ESI): m=z ¼ 185 [M þ H]. Anal. calcd. for
C7H11N3O3: C, 45.40; H, 5.99; N, 22.69%. Found: C, 45.11; H, 6.35; N, 23.00%.
3-(3-Benzyl-ureido)-2-formyl-acrylamide (4c). White solid; 1.92 g, yield:
78%; mp 190–192 ꢀC; IR (KBr): 3392, 3278, 3145, 2721, 1681, 1542, 1497, 1469,
1
1447, 1401, 1308, 1222 cmꢂ1; H NMR (300 MHz, DMSO): d ¼ 11.71 (d, J ¼ 12 Hz,
1H, -NH), 9.24 (s, 1H, -CHO), 8.88 (t, J ¼ 5.7 Hz, 1H, -NH), 8.26 (d, J ¼ 12 Hz, 1H,
-CH), 8.17 (bs, 1H, -NH), 7.56 (bs, 1H, -NH), 7.37 (m, 5H, -ArH), 4.37 (d,
J ¼ 5.4 Hz, 2H, -CH2); 13C NMR (75 MHz, DMSO): d ¼ 191.6, 167.1, 157.6, 151.7,
138.4, 128.3, 127.2, 127.0, 107.9, 43.3; MS (ESI): m=z ¼ 247 [M þ H]. Anal. calcd.
for C12H13N3O3: C, 58.29; H, 5.30; N, 16.99%. Found: C, 57.95; H, 5.55; N, 17.35%.

1584
M. G. GHAGARE ET AL.
2-Formyl-3-(3-phenyl-ureido)-acrylamide (4d). Yellow solid; 1.84 g, yield:
79%; mp 214–216 ꢀC; IR (KBr): 3455, 3290, 3081, 3024, 2741, 1741, 1670, 1619,
1544, 1447, 1380, 1289, 1243 cmꢂ1
;
1H NMR (300 MHz, DMSO): d ¼ 11.89 (d,
J ¼ 11.7 Hz, 1H, -NH), 10.62 (bs, 1H, -NH), 9.31 (s, 1H, -CHO), 8.34 (d, J ¼ 11.7 Hz,
1H, -CH), 8.19 (d, J ¼ 3 Hz, 1H, -NH), 7.66 (d, J ¼ 3 Hz, 1H, -NH), 7.54 (m, 5H,
ArH); 13C NMR (75 MHz, DMSO): d ¼ 191.5, 167.0, 156.5, 149.3, 142.2, 135.6,
132.4, 128.6, 125.3; MS (ESI): m=z ¼ 233 [M þ H]. Anal. calcd. for C11H11N3O3:
C, 56.65; H, 4.75; N, 18.02%. Found: C, 57.00; H, 4.53; N, 18.40%.
2-Formyl-3-(3-phenethyl-ureido)-acrylamide (4e). Yellow solid; 2.16 g,
yield: 83%; mp 180–182 ꢀC; IR (KBr): 3374, 3282, 3061, 3026, 2969, 1730, 1627,
1548, 1449, 1367, 1318, 1235 cmꢂ1
;
1H NMR (300 MHz, DMSO): d ¼ 11.55 (d,
J ¼ 12.3 Hz, 1H, -NH), 9.20 (s, 1H, -CHO), 8.44 (t, J ¼ 5.4 Hz, 1H, -NH), 8.20 (d,
J ¼ 12.3 Hz, 1H, -CH), 8.14 (d, J ¼ 3.0 Hz, 1H, -NH), 7.52(d, J ¼ 3.0 Hz, 1H, -NH),
7.31 (m, 5H, -ArH), 3.43 (q, J ¼ 7.2 Hz, 2H, -CH2), 2.79 (t, J ¼ 7.2 Hz, -CH2); 13C
NMR (75 MHz, DMSO): d ¼ 191.5, 167.1, 157.5, 151.5, 138.9, 128.5, 128.2, 126.1,
107.7, 41.0, 35.0; MS (ESI): m=z ¼ 261 [M þH]. Anal. calcd. for C13H15N3O3: C,
59.76; H, 5.79; N, 16.08%. Found: C, 58.92; H, 6.10; N, 16.24%.
General Procedure for the Synthesis of 5a–e
A mixture of 4a–e (1.5 g, 10 mmol) and t-BuOK (1.12 g, 10 mmol) in methanol
(50 ml) was heated to 55–60 ꢀC for 4–5 h (TLC monitoring). The solvent was
removed in vacuo at 50 ꢀC. The residue was suspended in water (30 ml), pH was
adjusted to 4–5 with acetic acid, and the solid was collected by filtration to give
1.23 g of 5a as a brown solid.
Selected Data
2-Oxo-1,2-dihydro-pyrimidine-5-carboxalic acid amide (5a). Yield: 89%;
mp 297–300ꢀC; IR (KBr): 3360, 3196, 3053, 2959, 2918, 2815, 1671, 1618, 1550, 1430,
1
1383, 1359, 1227 cmꢂ1; H NMR (300MHz, DMSO): d ¼ 12.32 (bs, 1H, -NH), 8.66
(s, 2H, -CH), 7.80 (bs, 1H, -NH), 7.36 (bs, 1H, -NH); 13C NMR (75 MHz, DMSO):
d ¼ 163.7, 155.7, 153.5, 135.0, 110.5; MS (ESI): m=z ¼ 139 [M þ H]. Anal. calcd. for
C5H5N3O2: C, 43.17; H, 3.62; N, 30.21%. Found: C, 43.38; H, 3.35; N, 29.88%.
1-Ethyl-2-oxo-1,2-dihydro-pyrimidine-5-carboxalic acid amide (5b). Yellow
solid; 1.53 g, yield: 92%; mp 176–178 ꢀC; IR (KBr): 3368, 3213, 2985, 2214, 1704,
1
1650, 1602, 1524, 1449, 1391, 1265 cmꢂ1; H NMR (300 MHz, DMSO): d ¼ 8.92
(d, J ¼ 3 Hz 1H, -CH), 8.72 (d, J ¼ 3 Hz 1H, -CH), 7.83 (bs, 1H, -NH), 7.41 (bs,
1H, -NH), 3.94 (q, J ¼ 7.1 Hz 2H, -CH2), 1.28 (t, J ¼ 6.9 Hz 3H, -CH3); 13C NMR
(75 MHz, DMSO): d ¼ 164.0, 163.5, 154.7, 150.9, 111.0, 46.4, 13.8; MS (ESI): m=z ¼
167 [M þ H]. Anal. calcd. for C7H9N3O2: C, 50.30; H, 5.43; N, 25.14%. Found: C,
50.75; H, 5.15; N, 24.89%.
1-Benzyl-2-oxo-1,2-dihydro-pyrimidine-5-carboxalic acid amide (5c).
Colorless solid; 2.17 g, yield: 95%; mp 224–226 ꢀC; IR (KBr): 3325, 3161, 2793,
1
2164, 1949, 1673, 1520, 1494, 1445, 1455, 1411, 1375, 1220, 1135 cmꢂ1; H NMR

NOVEL AND EFFICIENT SYNTHESIS OF PYRIMIDINE DERIVATIVES
1585
(300 MHz, DMSO): d ¼ 8.99 (d, J ¼ 3 Hz, 1H, -CH), 8.88 (d, J ¼ 3 Hz, 1H, -CH),
7.90 (bs, 1H, -NH), 7.47 (bs, 1H, -NH), 7.36 (m, 5H, -ArH), 5.11 (s, 2H, -CH2);
13C NMR (75 MHz, DMSO): d ¼ 164.4, 163.4, 154.8, 151.3, 135.6, 128.5, 127.9,
127.8, 111.3, 53.8; MS (ESI): m=z ¼ 229 [M þ H]. Anal. calcd. for C12H11N3O2: C,
62.87; H, 4.84; N, 18.33%. Found: C, 62.35; H, 4.50; N, 18.59%.
2-Oxo-1-phenyl-1,2-dihydro-pyrimidine-5-carboxylic acid amide (5d).
Colorless solid; 1.93 g, yield: 90%; mp 256–259 ꢀC; IR (KBr): 3303, 3142, 3057,
1
1892, 1685, 1515, 1454, 1435, 1372, 1284, 1178, 1133 cmꢂ1; H NMR (300 MHz,
DMSO): d ¼ 9.05 (d, J ¼ 3.3 Hz, 1H, -CH), 8.68 (d, J ¼ 3.3 Hz, 1H, -CH), 7.84 (bs,
1H, -NH), 7.58 (m, 5H, -ArH), 7.45 (bs, 1H, -NH). 13C NMR (75 MHz, DMSO):
d ¼ 165.0, 162.5, 155.0, 143.7, 134.5, 131.6, 129.0, 124.8, 111.7; MS (ESI): m=z
¼ 215 [M þ H]. Anal. calcd. for C11H9N3O2: C, 61.39; H, 4.22; N, 19.52%. Found:
C, 61.70; H, 4.51; N, 19.78%.
2-Oxo-1-phenethyl-1,2-dihydro-pyrimidine-5-carboxylic acid amide
(5e). Colorless solid; 2.25g, yield: 93%; mp 224–226 ꢀC; IR (KBr): 3369, 3157, 3029,
1
2167, 1674, 1514, 1452, 1416, 1381, 1325, 1267, 1191cmꢂ1; H NMR (300MHz,
DMSO): d ¼ 8.92 (d, J ¼ 3.0 Hz, 1H, -CH), 8.55 (d, J ¼ 3.0 Hz, 1H, -CH), 7.77 (bs,
1H, -NH), 7.37 (bs, 1H, -NH), 7.30 (m, 5H, -ArH), 4.13 (t, J ¼ 7.3 Hz, 2H, -CH2),
3.02 (t, J ¼ 7.3 Hz, 2H, -CH2); 13C NMR (75 MHz, DMSO): d ¼ 164.1, 163.4, 154.8,
151.4, 137.4, 128.7, 128.7, 128.4, 128.4, 126.5, 110.8, 52.5, 33.7; MS (ESI): m=z ¼ 243
[M þ H]. Anal. calcd. for C13H13N3O2: C, 64.19; H, 5.39; N, 17.27%. Found: C,
64.52; H, 5.64; N, 17.45%.
General Procedure for the Synthesis of 8a–d
A mixture of 5a (0.5 g, 3.5 mmol), K2CO3(0.48 g, 3.5 mmol), and 7a (0.99 g,
3.5 mmol) in DMF (5 ml) was stirred at 40–45 ꢀC for 8–10 h (TLC monitoring).
Reaction mass was then quenched in ice-cold water; the precipitated solid was
collected by filtration, washed with water, and recrystallized from ethanol to afford
8a (1.04 g, 86%).
Selected Data
1-[(2,4-Dichloro-phenylcarbamoyl)-methyl]-2-oxo-1,2-dihydro-pyrimidine-
5-carboxylic acid amide (8a). Off-white solid; yield: 86%; mp 240–245 ꢀC
(decom.); IR (KBr): 3280, 1677, 1620, 1583, 1520, 1476, 1386, 1326, 1290, 1255,
1195 cmꢂ1
;
1H NMR (300 MHz, DMSO): d ¼ 10.12 (bs, 1H, -NH), 9.01 (d,
J ¼ 3.0 Hz 1H, -CH), 8.74 (d, J ¼ 3.0 Hz 1H, -CH), 7.90 (bs, 1H, -NH), 7.79 (m,
3H, -ArH), 7.55 (bs, 1H, -NH), 4.95 (s, 2H, -CH2); 13C NMR (75 MHz, DMSO):
d ¼ 165.5, 164.7, 163.4, 154.9, 152.9, 133.4, 129.4, 128.9, 127.5, 126.7, 126.6, 111.0,
53.3; MS (ESI): m=z ¼ 341 [M þ H]. Anal. calcd. for C13H10Cl2N4O3: C, 45.77; H,
2.95; N, 16.42%. Found: C, 45.45; H, 2.72; N, 17.16%.
1-[(4-Chloro-3-trifluoromethyl-phenylcarbamoyl)-methyl]-2-oxo-1,2-
dihydro-pyrimidine-5-arboxylic acid amide (8b). Yellow solid; 1.11 g, yield:
83%; mp 285–287 ꢀC (decom.); IR (KBr): 3400, 3190, 3071, 1657, 1604, 1564,

1586
M. G. GHAGARE ET AL.
1522, 1489, 1429, 1391, 1321 cmꢂ1; 1H NMR (300 MHz, DMSO): d ¼ 10.89 (bs, 1H,
-NH), 9.04 (d, J ¼ 3.3 Hz, 1H, -CH), 8.75 (d, J ¼ 3.3 Hz, 1H, -CH), 7.94 (bs, 1H,
-NH), 7.78 (m, 3H, -ArH), 7.49 (bs, 1H, -NH), 4.82 (s, 2H, -CH2); 13C NMR
(75 MHz, DMSO): d ¼ 165.3, 164.7, 163.3, 154.8, 152.8, 137.7, 132.1, 132.0, 128.5,
124.2, 123.7, 117.4, 111.0, 53.5; MS (ESI): m=z ¼ 374 [M þ H]. Anal. calcd. for
C14H10ClF3N4O3: C, 44.88; H, 2.69; N, 14.95%. Found: C, 45.15; H, 3.00; N,
15.20%.
1-[(4-Chloro-phenylcarbamoyl)-methyl]-2-oxo-1,2-dihydro-pyrimidine-
5-carboxylic acid amide (8c). Brown solid; 0.96 g, yield: 87%; mp 215–220 ꢀC
(decom.); IR (KBr): 3291, 2927, 1666, 1599, 1524, 1492, 1401, 1304, 1250, 1092,
1013 cmꢂ1
;
1H NMR (300 MHz, DMSO): d ¼ 10.57 (bs, 1H, -NH), 9.03 (d,
J ¼ 3.3 Hz, 1H, -CH), 8.74 (d, J ¼ 3.3 Hz, 1H, -CH), 7.93 (bs, 1H, -NH), 7.63 (m,
4H, -ArH), 7.59 (bs, 1H, -NH), 4.80 (s, 2H, -CH2); 13C NMR (75 MHz, DMSO):
d ¼ 164.7, 163.4, 162.2, 154.9, 152.9, 137.3, 128.7, 127.1, 120.5, 111.0, 53.6; MS
(ESI): m=z ¼ 306 [M þ H]. Anal. calcd. for C13H11ClN4O3: C, 50.91; H, 3.62; N,
18.27%. Found: C, 51.28; H, 3.88; N, 18.49%.
1-[(4-Fluoro-phenylcarbamoyl)-methyl]-2-oxo-1,2-dihydro-pyrimidine-
5-carboxylic acid amide (8d). White solid; 0.93 g, yield: 90%; mp 252–255 ꢀC; IR
1
(KBr): 3369, 3206, 3163, 3094, 2951, 1655, 1612, 1578, 1512, 1426, 1389 cmꢂ1; H
NMR (300 MHz, DMSO): d ¼ 10.49 (bs, 1H, -NH), 9.02 (d, J ¼ 3.3 Hz 1H, -CH),
8.73 (d, J ¼ 3.3 Hz 1H, -CH), 7.92 (bs, 1H, -NH), 7.59 (m, 4H, -ArH), 7.47 (bs,
1H, -NH), 4.78 (s, 2H, -CH2); 13C NMR (75 MHz, DMSO): d ¼ 165.7, 164.4,
162.9, 155.0, 149.3, 134.5, 129.7, 128.2, 118.1, 111.0, 53.5; MS (ESI): m=z ¼ 290
[M þ H]. Anal. calcd. for C13H11FN4O3: C, 53.80; H, 3.82; N, 19.30%. Found: C,
54.14; H, 3.60; N, 19.55%.
ACKNOWLEDGMENTS
The authors gratefully acknowledge financial support of this project by the
University Grants Commission, New Delhi, India. We also thank Dr. V. B. Gaikwad
for his valuable cooperation.
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