4318-56-3

Basic information

• Product Name: 6-Chloro-3-methyluracil
• Synonyms: 3-METHYL-6-CHLOROURACIL;6-CHLORO-3-METHYLURACIL;6-chloro-3-methyl-2,4(1H,3H)-pyrimidinedione;6-chloro-3-methylpyrimidine-2,4(1H,3H)-dione;6-Chloro-3-dimethyl uracil;3-METHYL-6-CHLOROURACI;6-Chloro-3-Methyuracil;3-Methyl-6-chlorouracil, GC 97%
• CAS NO: 4318-56-3
• Molecular Formula: C₅H₅ClN₂O₂
• Molecular Weight: 160.56
• EINECS: 1308068-626-2
• Product Categories: Pyrimidine;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Intermediates
• Mol File: 4318-56-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 278-280°C (dec.)
• Boiling Point: 268.7 °C at 760 mmHg
• Flash Point: 116.3 °C
• Appearance: /
• Density: 0,896 gr/cm
• Vapor Pressure: 0.00101mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.16±0.40(Predicted)
• BRN: 511456
• CAS DataBase Reference: 6-Chloro-3-methyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-3-methyluracil(4318-56-3)
• EPA Substance Registry System: 6-Chloro-3-methyluracil(4318-56-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1992
• WGK Germany: 3
• Hazardous Substances Data: 4318-56-3(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

6-Chloro-3-methyluracil have been used in the synthesis of antibacterial agents as inhibitors of Helicobacter pylori glutamate racemase.

InChI:InChI=1/C5H5ClN2O2/c1-8-4(9)2-3(6)7-5(8)10/h2H,1H3,(H,7,10)

Synthetic route

1-methyl-2,4,6(1H,3H,5H)-pyrimidinetrione sodium salt → 3-methyl-6-chlorouracil (4318-56-3)

Conditions	Yield
With trichlorophosphate In water; acetonitrile at 8 - 80℃; for 2h; Temperature;	85.3%

1-methyl-2,4,6-pyrimidinetrione (2565-47-1) → 3-methyl-6-chlorouracil (4318-56-3)

Conditions	Yield
With water; trichlorophosphate at 80℃; for 4h;	81%
With water; trichlorophosphate at 80℃; for 2h;	80%
With trichlorophosphate at 0 - 80℃;	71.6%

6-hydroxy-3-methylpyrimidine-2,4(1H,3H)-dione (882872-13-1) → 3-methyl-6-chlorouracil (4318-56-3)

Conditions	Yield
With trichlorophosphate In acetonitrile at 120℃; for 0.333333h; Microwave irradiation;	80%

malonic acid (141-82-2) + N-Methylurea (598-50-5) → 3-methyl-6-chlorouracil (4318-56-3)

Conditions	Yield
Stage #1: malonic acid; N-Methylurea With acetic anhydride; acetic acid Stage #2: With trichlorophosphate

1-methyl-1H-imidazole (616-47-7) + 3-methyl-6-chlorouracil (4318-56-3) → 3-methyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)imidazolium chloride

Conditions	Yield
In chlorobenzene for 7h; Heating;	100%

3-methyl-6-chlorouracil (4318-56-3) → 6-hydrazinyl-3-methylpyrimidine-2,4(1H,3H)-dione (123506-41-2)

Conditions	Yield
With hydrazine hydrate In ethanol at 20 - 80℃;	100%
With hydrazine hydrate In ethanol at 80℃; for 1h;	100%
With hydrazine hydrate In ethanol at 80℃; for 1h; Inert atmosphere;	100%

3-methyl-6-chlorouracil (4318-56-3) + 2-(bromomethyl)-4-fluorobenzonitrile (421552-12-7) → 2-[(6-chloro-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]-4-fluorobenzonitrile (865759-24-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20 - 55℃; for 4h; Time; Temperature;	98.9%
Stage #1: 3-methyl-6-chlorouracil; 2-(bromomethyl)-4-fluorobenzonitrile In tetrahydrofuran at 40℃; for 0.25h; Stage #2: With sodium hydrogencarbonate; copper(II) acetylacetonate In tetrahydrofuran at 60℃; for 3h; Temperature; Reagent/catalyst;	98.93%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 107℃; for 2h; Solvent; Temperature; Reagent/catalyst;	96.6%

4-amino-N,N-dimethylaniline (99-98-9) + 3-methyl-6-chlorouracil (4318-56-3) → 6-(4-Dimethylamino-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion (83983-31-7)

Conditions	Yield
With sodium hydroxide for 0.5h;	98%
Heating;	92%

3-methyl-6-chlorouracil (4318-56-3) + para-fluorobenzylamine (140-75-0) → 6-(4-fluoro-benzylamino)-3-methyl-1H-pyrimidine-2,4-dione

Conditions	Yield
In butan-1-ol for 3h; Substitution; Heating;	97%

3-methyl-6-chlorouracil (4318-56-3) + 2-(bromomethyl)benzonitrile (22115-41-9) → 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile (865758-96-9)

Conditions	Yield
Stage #1: 3-methyl-6-chlorouracil With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 23℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 2-(bromomethyl)benzonitrile In tetrahydrofuran at 65℃; for 2h; Schlenk technique; Inert atmosphere;	96%
With 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine at 60 - 65℃; for 3h; Large scale;	96.42%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40 - 45℃; Solvent; Temperature;	95.8%

benzyl bromide (100-39-0) + 3-methyl-6-chlorouracil (4318-56-3) → 1-benzyl-6-chloro-3-methyl-1H-pyrimidine-2,4-dione (66400-16-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 12h; Reagent/catalyst; Temperature;	96%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 6h;

m-Anisidine (536-90-3) + 3-methyl-6-chlorouracil (4318-56-3) → 6-(3-Methoxy-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion (59776-23-7)

Conditions	Yield
With sodium hydroxide for 0.5h;	95%
Heating;	69%

thiophenol (108-98-5) + 3-methyl-6-chlorouracil (4318-56-3) → 3-methyl-6-(phenylthio)pyrimidine-2,4(1H,3H)-dione (69139-08-8)

Conditions	Yield
With potassium hydroxide In ethanol for 2h; Heating;	95%
Stage #1: 3-methyl-6-chlorouracil With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: thiophenol With potassium phosphate In N,N-dimethyl-formamide at 50℃; for 2h; Schlenk technique; Inert atmosphere;	72%

C5H14N2*2ClH + 3-methyl-6-chlorouracil (4318-56-3) → C10H18N4O2 (1186491-87-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;	95%

(4-fluorobenzyl)hydrazine dihydrochloride + 3-methyl-6-chlorouracil (4318-56-3) → C12H13FN4O2 (1186491-91-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;	95%

2-methylpropylhydrazine dihydrochloride (145295-89-2) + 3-methyl-6-chlorouracil (4318-56-3) → C9H16N4O2 (1186491-89-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;	95%

benzylhydrazine dihydrochloride (20570-96-1) + 3-methyl-6-chlorouracil (4318-56-3) → 3-methyl-6-(1-benzylhydrazino)uracil (58695-90-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;	95%

3-methyl-6-chlorouracil (4318-56-3) + ethyl hydrazine dihydrochloride → 6-(1-ethylhydrazinyl)-3-methylpyrimidine-2,4(1H,3H)-dione (144294-61-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;	95%

3-methyl-6-chlorouracil (4318-56-3) + 1-propylhydrazine dihydrochloride → C8H14N4O2 (1186491-90-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;	95%

3-methyl-6-chlorouracil (4318-56-3) + 1-butylhydrazine dihydrochloride → 6-(N-Butylhydrazino)-3-methyl-1H-pyrimidine-2,4-dione (729599-02-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;	95%

3-methyl-6-chlorouracil (4318-56-3) + para-methylbenzylamine (104-84-7) → 3-methyl-6-(4-methyl-benzylamino)-1H-pyrimidine-2,4-dione

Conditions	Yield
In butan-1-ol for 3h; Substitution; Heating;	94%

4-chlorobenzylamine (104-86-9) + 3-methyl-6-chlorouracil (4318-56-3) → 6-<(4-chlorobenzyl)amino>-3-methyluracil (73908-18-6)

Conditions	Yield
In butan-1-ol for 3h; Substitution; Heating;	93%
In butan-1-ol for 4h; Heating;	60%

N-methyl-p-aminophenol (150-75-4) + 3-methyl-6-chlorouracil (4318-56-3) → 6-(4-Hydroxy-N-methyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion (76837-72-4)

Conditions	Yield
at 145℃; for 0.5h;	93%

4-methoxy-benzylamine (2393-23-9) + 3-methyl-6-chlorouracil (4318-56-3) → 6-(4-Methoxy-benzylamino)-3-methyl-1H-pyrimidine-2,4-dione (73908-17-5)

Conditions	Yield
In butan-1-ol for 3h; Substitution; Heating;	93%

3-methyl-6-chlorouracil (4318-56-3) + p-methoxybenzyl chloride (824-94-2) → 6-chloro-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (916764-89-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;	93%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;	70%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;	66.7%

4-amino-o-xylene (95-64-7) + 3-methyl-6-chlorouracil (4318-56-3) → 6-(3,4-Dimethyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion (59776-24-8)

Conditions	Yield
With sodium hydroxide for 0.5h;	92%
at 160 - 170℃; for 0.166667h;	89%
With acetic acid; N,N-diethylaniline at 190℃; for 0.416667h;	88%
at 180 - 200℃; for 0.166667 - 0.25h;

n-Dodecylamine (124-22-1) + 3-methyl-6-chlorouracil (4318-56-3) → 6-(Dodecylamino)-3-methyluracil (83797-71-1)

Conditions	Yield
In butan-1-ol for 5h; Heating;	92%

3-methyl-6-chlorouracil (4318-56-3) + 4-chlorobenzohydroximoyl chloride (28123-63-9) → 3-(4-chlorophenyl)-6-methyl-5H-[1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione

Conditions	Yield
With triethylamine In methanol at 20℃; for 5h;	92%

3-methyl-6-chlorouracil (4318-56-3) + propargyl bromide (106-96-7) → 6-chloro-3-methyl-1-(prop-2-yn-1-yl)pyrimidine-2,4(1H,3H)-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux;	92%

N-hydroxy-4-methylbenzenecarboximidoyl chloride (36288-37-6) + 3-methyl-6-chlorouracil (4318-56-3) → 6-methyl-3-(p-tolyl)-5H-[1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione

Conditions	Yield
With triethylamine In methanol at 20℃; for 5h;	91%

(R)-piperidin-3-ylcarbamic acid tert-butyl ester (309956-78-3) + 3-methyl-6-chlorouracil (4318-56-3) → (R)-1-(1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-3-tert-butoxycarbonylaminopiperidine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 78 - 82℃; for 10h; Reagent/catalyst; Solvent;	91%

dmap (1122-58-3) + 3-methyl-6-chlorouracil (4318-56-3) → 4-(dimethylamino)-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)pyridinium chloride

Conditions	Yield
In various solvent(s) for 5h; Heating;	90%

methyl bromide (74-83-9) + 3-methyl-6-chlorouracil (4318-56-3) → 1,3-Dimethyl-6-chlorouracil (6972-27-6)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; Alkylation;	90%

3-methyl-6-chlorouracil (4318-56-3) + allyl bromide (106-95-6) → 1-allyl-6-chloro-3-methyl-1H-pyrimidine-2,4-dione (66400-17-7)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; Alkylation;	90%

Upstream product

• 882872-13-1 6-hydroxy-3-methylpyrimidine-2,4(1H,3H)-dione 
• 141-82-2 malonic acid 
• 598-50-5 N-Methylurea 
• 2565-47-1 1-methyl-2,4,6-pyrimidinetrione 
• 6945-56-8 6-hydroxy-3-methyl-2-methylthio-4(3H)-pyrimidinone 
• 89466-43-3 6-chloro-3-methyl-2-methylthio-4(3H)-pyrimidinone 

Downstream Products

• 83983-30-6 6-((4-hydroxyphenyl)amino)-3-methylpyrimidine-2,4(1H,3H)-dione 
• 73908-17-5 6-(4-Methoxy-benzylamino)-3-methyl-1H-pyrimidine-2,4-dione 
• 42747-84-2 3-methyl-6-(1-methylhydrazinyl)pyrimidine-2,4(1H,3H)-dione 
• 76896-61-2 6-(p-fluorophenyl)-3-methyluracil 
• 112069-53-1 6-(3-Bromo-phenylamino)-3-methyl-1H-pyrimidine-2,4-dione 
• 5759-79-5 3-methyl-6-(benzylamino)uracil 
• 133373-55-4 3-Methyl-6-o-tolylamino-1H-pyrimidine-2,4-dione 
• 5759-63-7 6-methylamino-3-methyluracil 
• 133373-65-6 6-(3,5-Bis-trifluoromethyl-phenylamino)-3-methyl-1H-pyrimidine-2,4-dione 
• 133373-71-4 6-(4-Chloro-3-trifluoromethyl-phenylamino)-3-methyl-1H-pyrimidine-2,4-dione 
• 133373-66-7 6-(3,5-Dimethoxy-phenylamino)-3-methyl-1H-pyrimidine-2,4-dione 
• 83983-28-2 6-(3-Dimethylamino-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion 
• 133373-69-0 6-(4-Chloro-3-methyl-phenylamino)-3-methyl-1H-pyrimidine-2,4-dione 
• 133373-67-8 6-(3-Chloro-4-methyl-phenylamino)-3-methyl-1H-pyrimidine-2,4-dione 

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