Alkylation of pyrimidine derivatives with ethylene chlorohydrin

Article abstract of DOI:10.1134/S1070428006110182

Alkylation of 6-methyluracil, 5-fluorouracil, uracil-5-ammonium sulfate, 5-hydroxyuracil, 5-hydroxy-6-methyluracil, 3,6-dimethyl-5-hydroxyuracil, and 1,3,6-trimethyl-5-hydroxyuracil with ethylene chlorohydrin in water-alcohol medium in the presence of KOH was investigated.

Full text of DOI:10.1134/S1070428006110182

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2006, Vol. 42, No. 11, pp. 1711−1714.  Pleiades Publishing, Inc. 2006.
Original Russian Text  V.P. Krivonogov, V.A. Myshkin, G.G. Kozlova, Yu.N. Chernyshenko, A.I. Savlukov, V.V. Plechev, R.B. Ibatullina,
I.B. Abdrakhmanov, L.V. Spirikhin, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 11, pp. 1723−1726.
Alkylation of Pyrimidine Derivatives with Ethylene Chlorohydrin
V. P. Krivonogov, V.A. Myshkin, G. G. Kozlova, Yu. N. Chernyshenko,
A. I. Savlukov, V. V. Plechev, R. B. Ibatullina, I. B.Abdrakhmanov,
and L. V. Spirikhin
Institute of Organic chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, 450054 Russia
e- mail: chemorg@anrb.ru
Received June 30, 2004
Abstract—Alkylation of 6-methyluracil, 5-fluorouracil, uracil-5-ammonium sulfate, 5-hydroxyuracil, 5-hydroxy-6-
methyluracil, 3,6-dimethyl-5-hydroxyuracil, and 1,3,6-trimethyl-5-hydroxyuracil with ethylene chlorohydrin in water-
alcohol medium in the presence of KOH was investigated.
DOI: 10.1134/S1070428006110182
Alkylation of uracil and 6-methyluracil with ethylene
chlorohydrin was reported in [1]. It was demonstrated
that the reaction gave rise either to O- or N-alkylated
products or to a mixture of both. Uracil reaction with
esters in DMSO in the presence of K2CO3 provided
mixtures of N-substituted uracils [2]. In the study of uracil
reaction with chlorohydrins in water in the presence of
NaOH also only the products of N-alkylation were
obtained [3].
Alkylation of 5-fluorouracil (II) with ethylene
chlorohydrin led to the formation of 1,3-bis(2-hydroxy-
ethyl)-5-fluorouracil (XI) in 97% yield as a thick light-
yellow fluid of Rf 0.77, and of crystalline 3-(2-hydroxy-
ethyl)-5- fluorouracil (XII) in 3% yield. By alkylation of
uracil-5-ammonium sulfate (III) 1,3-bis(2-hydroxyethyl)-
uracil-5-ammonium sulfate (XIII) was obtained, whose
hydrolysis with H2SO4 resulted in 1,3-bis(2-hydroxyethyl)-
5-hydroxyuracil (XIV). To elucidate the direction of
alkylation either at N1 or N3 atoms we measured the UV
spectra of compounds IX and XII at pH variation. It
was established that when pH of the medium changed
from 1 to 12 the absorption maximum suffered a red shift
of 18–23 nm characteristic of uracil substituted at N3 of
the ring [4].
In extension of the search for new pyrimidine
derivatives with possible immunotropic, antiphlogistic, and
antiradical action we investigated alkylation of 6-
methyluracil (I), 5-fluorouracil (II), uracil-5-ammonium
sulfate (III), 5-hydroxyuracil (IV), 5-hydroxy-6-
methyluracil (V), 3,6-dimethyl-5-hydroxyuracil (VI), and
1,3,6-trimethyl-5-hydroxyuracil (VII) with ethylene
chlorohydrin (VIII) in a water-alcohol medium in the
presence of KOH.
To distinguish the alkylation direction in the uracil
derivatives in position 1 or 3 we also used the 1H NMR
spectra. Thus with a substituent in position 3 the signal
of N1H proton appears in the region 8–9 ppm, whereas
with a substituent in position 1 the resonance of N3H
proton is observed in the region 10–11 ppm.
Alkylation of 6-methyluracila (I) with ethylene
chlorohydrin (VIII) in a water-alcohol medium in the
presence of KOH provided 3-(2-hydroxyethyl)-6-methyl-
uracil (IX) and 1,3-bis(2-hydroxyethyl)-6-methyluracil (X)
that were isolated in a pure state by recrystallization from
alcohol in 10 and 50% yield respectively. N-(Hydroxy-
ethyl)-6-methyluracils obtained are crystalline substances
well soluble in water and moderately soluble in alcohol.
Their structure was proved by comparison with the
published melting point [2], and also by UV spectra.
In reaction of 5-hydroxyuracil (IV) and 5-hydroxy-6-
methyluracil (V) with ethylene chlorohydrin the alkylation
was found to occur simultaneously in all three positions
1, 3, and 5. On alkylating 5-hydroxyuracil (IV) with
ethylene chlorohydrin we obtained a mixture whose
repeated recrystallization permitted isolation of 1,3-bis(2-
hydroxyethyl)-5-(2-hydroxyethoxy)uracil (XV) in 77%
1711

KRIVONOGOV et al.
1712
yield and 1,3-bis(2-hydroxyethyl)-5-hydroxyuracil (XIV).
Alkylation of 5-hydroxy-6-methyluracil (V) resulted in a
mixture of compounds that was subjected to repeated
recrystallization to isolate in pure state 1,3-bis(2-
hydroxyethyl)-5-(2-hydroxyethoxy)-6-methyluracil (XVI)
in 50% yield (mp 136-–138°C), well soluble in water,
alcohol, and chloroform; 1,3-bis(2-hydroxyethyl)-5-
hydroxy-6-methyluracil (XVII) in 20% yield (mp 227–
230°C); and 3-(2-hydroxyethyl)-5-(2-hydroxyethoxy)-6-
methyluracil (XVIII) in 10% yield as a thick fluid.
the absorption band of a hydroxy group involved in
a hydrogen bond was observed at 3400 cm–1.
In the 13C NMR spectra of all compounds the carbon
atoms of the uracil fragment appeared as usual signals
at 164 (C4), 157 (C2), 153 (C6) ppm, also signals were
observed in the region 13–14 (CH3C6), and 98–102 (C5)
ppm.
EXPERIMENTAL
UV spectra of solutions with concentration 10–5%
were measured on a spectrometer Specord M-400 in the
range 200–350 nm in a cell 19 mm thick. IR spectra were
recorded from mulls of compounds in mineral oil or from
liquid films on a spectrophotometer UR-20 with prisms
O
O
Cl
R2
O
R3
R4
R6
O
R7
R8
OH, KOH
VIII
N
N
N
N
1
of NaCl and LiF. H and 13C NMR spectra were
R1
_
R5
registered from 1% (1H) or 10–20% (13C) solutions in
D2O on a spectrometer Bruker AM (at 300 and 75 MHz
respectively), internal reference HMDS. Melting points
_
I VII
IX XXI
R1 = R2 = R3 = H, R4 = Me (I); R1 = R2 = R4 = H, R3 = F (II),
OSO3NH4 (III), OH (IV); R1 = R2 = H, R3 = OH, R4 = Me
(V); R1 = H, R2 = R4 = Me, R3 = OH (VI); R1 = R2 = R4 = Me,
R3 = OH (VII); R5 = R7 = H, R6 = CH2CH2OH, R8 = Me (IX);
R5 = R6 = CH2CH2OH, R7 = H, R8 = Me (X), R7 = F, R8 = H
(XI); R5 = R8 = H, R6 = CH2CH2OH, R7= F (XII); R5 = R6 =
CH2CH2OH, R8 = H, R7 = OSO3NH4 (XIII), OH (XIV),
OCH2CH2OH (XV); R5 = R6 = CH2CH2OH, R8 = Me, R7=
OCH2CH2OH (XVI), OH (XVII); R5 = H, R6 = CH2CH2OH,
R7 = OCH2CH2OH, R8 = Me (XVIII); R5= CH2CH2OH, R6=
R8 = Me, R7 = OCH2CH2OH (XIX), OH (XX); R5 = R6 =
R8 = Me, R7 = OCH2CH2OH (XXI).
..
were measured on a Boetius heating block. Elemental
analyses were carried out on CHN Analyzer M-185Β.
The monitoring of reaction progress and checking the
homogeneity of compounds obtained was performed by
TLC on Silufol UV-254 plates, eluent ethanol–ammonia,
4:1, development under UV irradiation or in iodine vapor.
3-(2-Hydroxyethyl)-6-methyluracil (IX) and
1,3-bis(2-hydroxyethyl)-6-methyluracil (X). To
126 g (0.1 mol) of 6-methyluracil was poured 800 ml of
water and 100 ml of ethanol, 2 mol of 82% powdered
KOH was added, and within 30 min at room temperature
was added 200 g (2.5 mol) of ethylene chlorohydrin. The
reaction mixture was gradually brought to boiling by
heating on a water bath, and it was stirred for 4–6 h till
the pH of the mixture turned neutral or slightly acidic
(pH 6–7). Then water was distilled off from the reaction
mixture under a vacuum of an oil pump, the separated
crystals were filtered off, washed with hot acetone,
acetone and the mother liquor were combined, and
acetone was distilled off. The thick mass obtained
(164 g) was dissolved in 300 ml of 2-propanol, and the
product was precipitated from the solution by hexane
(400 ml). The underlayer was separated, on distilling off
the solvent and azeotropic drying we obtained 100 g (50%)
of compound (X), mp 110–112°C (111–112°C [1]). IR
spectrum, ν, cm– 1: 800, 1060–1280 (=N–), 1370 [δs
(CH3)], 1470 (CH2, CH3), 1600, 1650, 1690 (C=O,
On alkylating 3,6-dimethyl-5-hydroxyuracil (VI) with
ethylene chlorohydrin under these conditions we obtained
1-hydroxyethyl-5-(2-hydroxyethoxy)-3,6-dimethyluracil
(XIX) and 1-hydroxyethyl-5-hydroxy-3,6-dimethyluracil
(XX). The alkylation of 1,3,6-trimethyl-5-hydroxyuracil
(VII) with ethylene chlorohydrin gave 1,3,6-trimethyl-5-
(2-hydroxyethoxy)uracil (XXI) in 80% yield, mp 280°C,
Rf 0.8.
The structure of compounds obtained was proved by
1
IR, UV, H and 13C NMR spectra, and also by the
elemental analyses.
In the IR spectra of all compounds absorption bands
were present in the region 1620–1720 cm–1 characteristic
of vibrations of the pyrimidine fragment [ν(C–O, NC–
O)]. The absorption bands in the region 1060–1240 cm–1
are common in spectra of compounds whose molecules
contain a tertiary nitrogen; absorption bands in the region
3300–3500 cm–1 are due to the stretching vibrations of
the O–H and N–H bonds. In the spectra of all compounds
1
=NC=O), 2860, 2940 (CH), 3500 (OH). H NMR
spectrum, δ, ppm: 2.07 s (3H, CH3), 3.61 t (2H, C8H2,
J 5.8 Hz), 3.68 t (2H, C7H2, J 5.8 Hz), 3.73 d (2H, C10H2,
J 5.8 Hz), 3.9 t (2H, C9H2, J 5.8 Hz), 4.8 s (2H, OH).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006

ALKYLATION OF PYRIMIDINE DERIVATIVES WITH ETHYLENE CHLOROHYDRIN
1713
13C NMR spectrum, δ, ppm: 22.27 (CH3), 45.61 (C9),
49.79 (C7), 61.19 (C8), 61.61 (C10), 103.11 (C5), 155.0
(C6), 158.25 (C2), 167.45 (C4). Found, %: C 50.43;
H 6.34; N 13.8. C9H14N2O4. Calculated, %: C 50.46;
H 6.59; N 13.08. From the upper organic layer the
solvents were distilled off, the residue was dissolved in
alcohol, the precipitated crystals were filtered off and
dried. We obtained 17 g (10%) of compound IX, mp 205–
206°C (205– 206°C [1]). IR spectrum, ν, cm– 1: 790,
880, 1080–1260 (=N–), 1360, 1390 [δs (CH3)], 1480
(CH2, CH3), 1600, 1650, 1710 (C=O, NC=O), 2870, 2950
(CH), 3100 (NH). Found, %: C 49.96; H 6.16; N 16.00.
C7H10N2O3. Calculated, %: C 49.40; H 5.92; N 16.46.
hydroxy-6-methyluracil (XVII), and 3-(2-hydroxy-
ethyl)-5-(2-hydroxyethoxy)-6-methyluracil (XVIII).
To 127.8 g (0.9 mol) of 5-hydroxy-6-methyluracil was
powred 800 ml of water, 174 g (2.85 mol) of powdered
KOH was added, and within 20 min was added 230 g
(2.88 mol) of ethylene chlorohydrin (the process occurred
with heat evolution). The reaction mixture was brought
to boiling by heating on a water bath and stirred for 4–
6 h. On cooling the reaction mixture was acidified to pH
6–7 with 1–2 ml of concn. HCl, water was distilled off
under a reduced pressure (50–100 mm Hg) at the bath
temperature 80°C. The precipitated crystals were filtered
off, washed with hot acetone to get in residue KCl.
Acetone was distilled off from the mother liquor, the
residue crystallized on standing. 165 g of crystals
separated by filtration were heated in 350 ml of ethanol
till they dissolved, the insoluble residue was filtered off
through a glass frit. On cooling, filtration, and drying we
obtained 46 g (20%) of compound XVII, mp 227–230°C.
IR spectrum, ν, cm–1: 780, 1060–1270 (=N–), 1385
[δs (CH3)], 1460 (CH2, CH3), 1600, 1650, 1690, 1710
(C=O, NC=O), 2860, 2940 (CH), 3560 (OH). 1H NMR
spectrum, δ, ppm: 1.89 s (3H, CH3), 3.60 t (2H, C7H2,
J 5.8 Hz), 3.65 d (2H, C8H2, J 5.8 Hz), 3.73 d (2H, C10H2,
J 5.8 Hz), 3.97 t (2H, C9H2, J 5.8 Hz), 6.8 s (3H, OH).
13C NMR spectrum, δ, ppm: 12.20 (CH3), 44.61 (C9),
52.79 (C7), 58.19 (C8), 60.61 (C10), 130.00 (C5), 141.0
(C6), 150.25 (C2), 160.45 (C4). Found, %: C 47.06;
H 6.09; N 11.88. C8H14N2O5. Calculated, %: C 46.95;
H 6.13; N 12.17. From the ethanolic mother liquor crystals
precipitated on standing, they were filtered off and dried
to obtain 138.4 g (50%) of compound XVI, mp 136–
138°C. IR spectrum, ν, cm–1: 780, 1050–1280 (=N–),
1379 [δs (CH3)], 1470 (CH2, CH3), 1600, 1650, 1690,
1710 (C=O, NC=O), 2860, 2960 (CH), 3600 (OH).
1H NMR spectrum, δ, ppm: 1.86 s (3H, CH3), 3.59 t
(2H, C7H2, J 5.8 Hz), 3.65 d (2H, C8H2, J 5.8 Hz),
3.73 d (2H, C10H2, J 5.8 Hz), 3.91 d (2H, C11H2, J 5.8 Hz),
3.97 t (2H, C9H2, J 5.8 Hz), 4.0 d (2H, C12H2, J 5.8 Hz),
4.96 s (3H, OH). 13C NMR spectrum, δ, ppm: 16.00
(CH3), 45.60 (C9), 52.79 (C7), 58.19 (C8), 60.60 (C10),
63.00 (C12), 65.00 (C11), 129.11 (C5), 142.45 (C6), 149.00
(C2), 161.85 (C4). Found, %: C 48.45; H 6.61; N 10.77.
C11H19N2O6. Calculated, %: C 48.17; H 6.61; N 10.21.
The residues of the mother liquors in acetone and ethanol
were combined , the solvents were distilled off to obtain
18.6 g (10%) of compound XVIII as a thick fluid, Rf
0.76. IR spectrum, ν, cm–1: 790, 880, 1080–1260 (=N–),
1360, 1390 [δs (CH3)], 1480 (CH2, CH3), 1600, 1650,
1710 (C=O, NC=O), 2870, 2950 (CH), 3100 (NH), 3490
1,3-Bis(2-hydroxyethyl)-5-fluorouracil (XI) and
3-(2-hydroxyethyl)-5-fluorouracil (XII) were prepared
analogously to compound X from 6.51 g (0.065 mol) of
5-fluorouracil, 6.8 g of KOH in 40 ml of water and 20 ml
of alcohol, and of 10.6 g (0.125 mol) of ethylene chloro-
hydrin. We obtained 11.6 g of thick light-brown fluid which
was dissolved in 30 ml of acetone, The precipitated
crystals were filtered off to obtain 1.2 g (3%) of
compound XII, mp 138–140°C. UV spectrum (ethanol):
λ
min 243, λmax277 nm. IR spectrum, ν, cm– 1: 800, 1072–
1270 (=N–), 1384 [δs (CH3)], 1460 (CH2, CH3), 1654,
1678, 1702 (C=O, NC=O), 2920, 2998 (CH), 3500 (OH).
1H NMR spectrum, δ, ppm: 3.75 t (2H, C10H2, J 5.8 Hz),
3.96 t (2H, C9H2, J 5.8 Hz), 5.04 (1H, OH), 7.56 d (1H,
C6H, JHF 8 Hz), 8.39 s (1H, N1H). 13C NMR spectrum,
δ, ppm: 42.74 (C9), 60.30 (C10), 125.75 (C5, JCF 251 Hz),
142.60 (C6, JCF 20 Hz), 152.50 (C2), 162.45 (C4, JCF 20
Hz). Found, %: C 41.00; H 4.40; F 10.5; N 14.60.
C6H7FN2O3. Calculated, %: C 41.38; H 4.05; F 10.91; N
15.08. On removing acetone from the filtrate we obtained
10 g (97%) of compound XI as a thick light-yellow fluid,
Rf 0.77. UV spectrum (ethanol): λmin 247.20, λmax278
nm. IR spectrum, ν, cm– 1: 784, 820, 850, 880, 922, 952,
1018– 1270 (=N–), 1384 [δs (CH3)], 1460 (CH2, CH3),
1635, 1654, 1684, 1714 (C=O, NC=O), 2890, 2932, 2968,
2998 (CH), 3334, 3376, 3470 (OH). 1H NMR spectrum,
δ, ppm: 3.72 t (6H, C7H2, C8H2, C10H2, J 5.8 Hz), 3.99 t
(2H, C9H2, J 5.8 Hz), 5.15 (2H, OH), 7.53 d (1H, C6H,
J
HF 8 Hz). 13C NMR spectrum, δ, ppm: 43.34 (C9), 54.39
(C7), 59.50 (C8), 60.31 (C10), 130.54 (C5, JCF 251 Hz),
140.30 (C6, JCF 20 Hz), 150.50 (C2), 161.40 (C4,
J
CF 20 Hz). Found, %: C 43.52; H 5.50; F 8.30; N 11.85.
C8H11FN2O4. Calculated, %: C 44.00; H 5.05; F 8.70;
N 12.13.
1,3-Bis(2-hydroxyethyl)-5-(2-hydroxyethoxy)-6-
methyluracil (XVI), 1,3-bis(2-hydroxyethyl)-5-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006

KRIVONOGOV et al.
1714
OH). 13C NMR spectrum, δ, ppm: 12.22 (CH3C6), 28.15
(CH3N3), 51.40 (C7), 58.00 (C8), 130.40 (C5), 142.45 (C6),
150.50 (C2), 162.40 (C4). Found, %: C 47.65; H 5.90; N
13.63. C8H12N2O4. Calculated, %: C 47.99; H 6.04; N
13.99.
1
(OH). H NMR spectrum, δ, ppm: 2.01 s (3H, CH3),
3.73 d (2H, C10H2, J 5.8 Hz), 3.95 t (2H, C9H2, J 5.8 Hz),
7.87 s (2H, OH), 9.05 (1H, N1H). 13C NMR spectrum,
δ, ppm: 13.66 (CH3), 42.37 (C9), 60.31 (C10), 130.12 (C5),
137.30 (C6), 157.50 (C2), 163.35 (C4). Found, %:
C 45.30; H 5.87; N 14.67. C7H10N2O4. Calculated, %:
C 45.16; H 5.41; N 15.04.
1,3,6-Trimethyl-5-(2-hydroxyethoxy)uracil (XXI)
was obtained in a similar way as compound XIX from
3.0 g (0.017 mol) of 1,3,6-trimethyl-5-hydroxyuracil (VI),
0.85 g (0.017 mol) of KOH in 10 ml of water and 10 ml
of ethanol, and of 1.5 ml (0.018 mol) of ethylene
chlorohydrin. We obtained 3.0 g (82%) of compound XXI,
mp 280°C, Rf 0.80. IR spectrum, ν, cm–1: 778, 826, 850,
1072, 1080–1252 (=N–), 1348, 1390 [δs (CH3)], 1456
(CH2, CH3), 1654, 1714 (C=O, NC=O), 2854, 2920 (CH),
1-Hydroxyethyl-5-(2-hydroxyethoxy)-3,6-
dimethyluracil (XIX) and 1-hydroxyethyl-5-hydroxy-
3,6-dimethyluracil (XX) were obtained in the same
fashion as compound X from 15.2 g (0.1 mol) of 3,6-di-
methyl-5-hydroxyuracil (V), 20.13 g (0.25 mol) of
ethylene chlorohydrin, 12.3 g (0.22 mol) of KOH in
80 ml of water and 40 ml of ethanol. We obtained 14.0 g
(57%) of compound XIX as thick light-yellow fluid,
Rf 0.70. UV spectrum (ethanol): λmin 247.20, λmax278
nm. IR spectrum, ν, cm–1: 712, 760, 778, 886, 1048, 1080–
1258 (=N–), 1354, 1384 [δs (CH3)], 1456 (CH2, CH3),
1636, 1654, 1684, 1696, 1714 (C=O, NC=O), 2870, 2950
1
3244, 3328, 3442 (OH). H NMR spectrum, δ, ppm:
1.84 s (3H, CH3C6), 3.30 s (3H, CH3N1), 3.43 s (3H,
CH3N3), 3.92 t (4H, C11H2, C12H2, J 6.9 Hz), 5.25 s
(1H, OH). 13C NMR spectrum, δ, ppm: 11.50 (CH3C6),
28.45 (CH3N1), 28.85 (CH3N3), 63.00 (C12), 64.70 (C11),
126.40 (C5), 142.45 (C6), 150.50 (C2), 161.80 (C4).
Found, %: C 50.10; H 6.70; N 12.68. C9H14N2O4.
Calculated, %: C 50.46; H 6.59; N 13.08.
1
(CH), 3100 (NH), 3490 (OH). H NMR spectrum, δ,
ppm: 1.86 s (3H, CH3C6), 3.42 s (3H, CH3N3), 3.59 t
(2H, C7H2, J 5.8 Hz), 3.66 t (2H, C8H2, J 5.8 Hz), 3.90 t
(2H, C11H2, J 6.9 Hz), 3.99 t (2H, C12H2, J 6.9 Hz),
4.93 s (2H, OH). 13C NMR spectrum, δ, ppm: 12.66
(CH3C6), 28.85 (CH3N3), 51.40 (C7), 58.00 (C8), 63.00
(C12), 64.60 (C11), 127.12 (C5), 142.45 (C6), 157.50 (C2),
162.35 (C4). Found, %: C 48.80; H 6.60; N 11.10.
C10H16N2O5. Calculated, %: C 49.15; H 6.60; N 11.47.
We also obtained 8.8 g (44%) of compound XX, mp
146°C, Rf 0.81. UV spectrum (ethanol): λmin 242.50,
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λ
max 276.50 nm. IR spectrum, ν, cm–1: 712, 760, 778,
886, 1048, 1080–1258 (=N–), 1354, 1384 [δs (CH3)], 1456
(CH2, CH3), 1636, 1654, 1684, 1696, 1714 (C=O, NC=O),
1
2870, 2950 (CH), 3100 (NH), 3490 (OH). H NMR
spectrum, δ, ppm: 1.89 s (3H, CH3C6), 3.43 s (3H,
CH3N3), 3.59 t (4H, C7H2, C8H2, J 5.8 Hz), 4.93 s (2H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006