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5909-24-0

Basic Information
CAS No.: 5909-24-0
Name: Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate
Article Data: 16
Molecular Structure:
Molecular Structure of 5909-24-0 (Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate)
Formula: C8H9ClN2O2S
Molecular Weight: 232.691
Synonyms: 2-Methylthio-4-chloro-5-ethoxycarbonylpyrimidine;4-Chloro-2-methanethiopyrimidine-5-carboxylic acid ethyl ester;4-Chloro-2-methylsulfanylpyrimidine-5-carboxylic acid ethyl ester;4-Chloro-5-carbethoxy-2-methylthiopyrimidine;4-Chloro-5-ethoxycarbonyl-2-methylthiopyrimidine;
EINECS: 227-619-0
Density: 1.37 g/cm3
Melting Point: 60-63 °C(lit.)
Boiling Point: 335.7 °C at 760 mmHg
Flash Point: 156.83 °C
Appearance: off white to light yellow solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 77.38000
LogP: 2.02860
Synthetic route
53554-29-3

ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate

5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride at 60℃; for 3h;92%
With N,N-diethylaniline; trichlorophosphate for 5h; Heating / reflux;77%
With trichlorophosphate In acetonitrile for 6h; Reagent/catalyst; Reflux;77%

sodium 5-(ethoxycarbonyl)-2-(methylthio)-4-oxo-4H-pyrimidin-3-ide

5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: sodium 5-(ethoxycarbonyl)-2-(methylthio)-4-oxo-4H-pyrimidin-3-ide With thionyl chloride In N,N-dimethyl-formamide; toluene at 20 - 30℃; for 0.5h; Large scale;
Stage #2: With trichlorophosphate In N,N-dimethyl-formamide; toluene at 55 - 65℃; for 1.5h; Large scale;
84.5%
With trichlorophosphate for 3h; Reflux;
With trichlorophosphate at 0℃; for 5h; Reflux;
53554-29-3

ethyl 3,4-dihydro-2-methylthio-4-oxopyrimidine-5-carboxylate

5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride
With trichlorophosphate
With trichlorophosphate at 100℃; for 3h;
87-13-8

diethyl 2-ethoxymethylenemalonate

5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: EtONa / ethanol
2: POCl3
View Scheme
Multi-step reaction with 2 steps
1: aqueous KOH
2: POCl3
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water / 0.08 h / 20 °C
1.2: 24 h / 20 °C
2.1: trichlorophosphate / 3 h / Reflux
View Scheme
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

74-89-5

methylamine

76360-82-2

4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
In ethanol; dichloromethane at 0℃; for 0.5h;100%
With triethylamine In tetrahydrofuran at 50℃;100%
at 0℃; for 0.5h;100%
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

117147-06-5

ethyl 4-hydrazinyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 0℃; for 1h;100%
With hydrazine hydrate In ethanol at 0℃; for 1h;91.8%
With hydrazine hydrate In ethanol at 0 - 20℃; for 1h;85.71%
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

1003-03-8

Cyclopentamine

211245-62-4

4-cyclopentylamino-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane for 0.75h; Heating / reflux;97%
With triethylamine In tetrahydrofuran at 20℃; for 1h;96.1%
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

115514-77-7

(3-chloro-4-methoxyphenyl)methanamine

330785-81-4

ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;100%
With triethylamine In acetone at 20℃; for 3h;87%
With triethylamine In dichloromethane at 20℃; for 10h;76%
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

60295-21-8

N'-cyclohexyl-hydrazine carboxylic acid tert-butyl ester

900502-62-7

C19H30N4O4S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;100%
With triethylamine In tetrahydrofuran at 20℃;100%
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

1410975-83-5

N-(((2S,4R)-4-hydroxypyrrolidin-2-yl)methyl)-2-nitrobenzenesulfonamide

1410975-85-7

ethyl 4-((2S,4R)-4-hydroxy-2-((2-nitrophenylsulfonamido)methyl)pyrrolidin-1-yl)-2-(methylthio)pyrimidine-5-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 1.5h;100%
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    Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate

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Specification

The Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate, with the CAS registry number 5909-24-0 and EINECS registry number 227-619-0, has the systematic name of ethyl 4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxylate. And the molecular formula of this chemical is C8H9ClN2O2S. It is a kind of off white to light yellow solid, and should keep cold. In addition, it is a pyrimidine derivative, and used as inhibitor of Streptococcus faecium, Lactobacillus casei, and Pediococcus cerevisiae.

The physical properties of Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate are as following: (1)ACD/LogP: 1.95; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.945; (4)ACD/LogD (pH 7.4): 1.945; (5)ACD/BCF (pH 5.5): 17.719; (6)ACD/BCF (pH 7.4): 17.719; (7)ACD/KOC (pH 5.5): 272.428; (8)ACD/KOC (pH 7.4): 272.428; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 77.38 Å2; (13)Index of Refraction: 1.568; (14)Molar Refractivity: 55.559 cm3; (15)Molar Volume: 169.735 cm3; (16)Polarizability: 22.025×10-24cm3; (17)Surface Tension: 57.906 dyne/cm; (18)Density: 1.371 g/cm3; (19)Flash Point: 156.83 °C; (20)Enthalpy of Vaporization: 57.879 kJ/mol; (21)Boiling Point: 335.707 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate: It can react with tert-butyl hydroperoxide to produce 4-tert-butylperoxy-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester. This reaction will need reagent Bariumoxid, and the solvent petroleum ether. The reaction time is 2 hours with temperature of 0°C, and the yield is about 62%.

Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate can react with tert-butyl hydroperoxide to produce 4-tert-butylperoxy-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: CCOC(=O)c1cnc(nc1Cl)SC
(2)InChI: InChI=1/C8H9ClN2O2S/c1-3-13-7(12)5-4-10-8(14-2)11-6(5)9/h4H,3H2,1-2H3
(3)InChIKey: SNNHLSHDDGJVDM-UHFFFAOYAH