6972-27-6

Basic information

• Product Name: 6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione
• Synonyms: 1,3-Dimethyl-4-chlorouracil;2,4(1H,3H)-Pyrimidinedione, 6-chloro-1,3-dimethyl-;1,3-DIMETHYL-6-CHLOROURACIL;6-CHLORO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE;6-CHLORO-1,3-DIMETHYLURACIL;6-CHLORO-1,3-DIMETHYL-2,4(1H,3H)-PYRIMIDINEDIONE;AURORA KA-4432;4-Chloro-1,3-dimethyluracil
• CAS NO: 6972-27-6
• Molecular Formula: C₆H₇ClN₂O₂
• Molecular Weight: 174.58
• EINECS: 230-205-2
• Product Categories: Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 6972-27-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 109-113 °C
• Boiling Point: 224.6 °C at 760 mmHg
• Flash Point: 89.6 °C
• Appearance: white or light white crystal powder
• Density: 1.4926 (rough estimate)
• Vapor Pressure: 0.0906mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: -3.53±0.40(Predicted)
• Water Solubility: soluble
• BRN: 144393
• CAS DataBase Reference: 6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione(6972-27-6)
• EPA Substance Registry System: 6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione(6972-27-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6972-27-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow flakes or powder

Uses

6-Chloro-1,3-dimethyluracil is a nucleobase constitute of nucleic acid. An intermediate for the synthesis of substituted uracils and derivatives.

InChI:InChI=1/C6H7ClN2O2/c1-8-4(7)3-5(10)9(2)6(8)11/h3H,1-2H3

Synthetic route

1,3-dimethylbarbituric acid (769-42-6) → 1,3-Dimethyl-6-chlorouracil (6972-27-6)

Conditions	Yield
With water; trichlorophosphate Heating;	93%
With water; trichlorophosphate for 6h; Reflux; Large scale;	92.3%
With trichlorophosphate

6-chlorouracil (4270-27-3) + methyl bromide (74-83-9) → 1,3-Dimethyl-6-chlorouracil (6972-27-6)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 20℃; for 48h;	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%

edaravone (89-25-8) + 6-chloro-5-formyl-1,3-dimethyluracil (35824-85-2) → 1,3-Dimethyl-6-chlorouracil (6972-27-6) + 1-phenyl-3-methyl-4-(1-phenyl-3-methyl-5-oxo-4-pyrazolylidene)methylene-5-pyrazolone (4702-90-3)

Conditions	Yield
With piperidine In ethanol at 20℃; for 0.5h;	A 75% B n/a

6-chlorouracil (4270-27-3) + methyl iodide (74-88-4) → 1,3-Dimethyl-6-chlorouracil (6972-27-6)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 23℃; for 3h; Schlenk technique; Inert atmosphere;	52%

6-chloro-2,4-dimethoxypyrimidine (6320-15-6) + methyl iodide (74-88-4) → 1,3-Dimethyl-6-chlorouracil (6972-27-6)

Conditions	Yield
at 90℃;

6-Amino-1,3-dimethylbarbituric acid (6642-31-5) → 1,3-Dimethyl-6-chlorouracil (6972-27-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous HCl 2: POCl3 View Scheme

6-chlorouracil (4270-27-3) + methyl halide → 1,3-Dimethyl-6-chlorouracil (6972-27-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 70℃; for 3h;

methanol (67-56-1) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → 6-methoxy-1,3-dimethyluracil (4097-20-5)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 2h; Ambient temperature;	100%

propan-1-ol (71-23-8) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → 1,3-Dimethyl-6-propoxy-1H-pyrimidine-2,4-dione (93767-18-1)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 2h; Ambient temperature;	100%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + ethanol (64-17-5) → 1,3-dimethyl-6-ethoxyuracil (93787-99-6)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 2h; Ambient temperature;	100%
With sodium carbonate for 28h; Reflux;	96%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + pentan-1-ol (71-41-0) → 1,3-Dimethyl-6-pentyloxy-1H-pyrimidine-2,4-dione (93767-19-2)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 2h; Ambient temperature;	100%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + allyl alcohol (107-18-6) → 1,3-dimethyluracil-6-allyl ether (93767-20-5)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 1.5h; Ambient temperature;	100%
With sodium for 2h; Heating;	63.3%
With sodium at 30 - 40℃; for 0.5h;	57.2%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + ethanethiol (75-08-1) → 6-Ethylsulfanyl-1,3-dimethyl-1H-pyrimidine-2,4-dione (35218-96-3)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 2.5h; Ambient temperature;	100%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + benzyl alcohol (100-51-6) → 6-Benzyloxy-1,3-dimethyl-1H-pyrimidine-2,4-dione (93767-21-6)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 2h; Ambient temperature;	100%

naphthalene (91-20-3) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → 6-methoxy-1,3-dimethyluracil (4097-20-5)

Conditions	Yield
In methanol at 20℃; for 1h; UV-irradiation;	100%

2,3-Dimethyl-2-butene (563-79-1) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → 1,1,2,2,3,5-hexamethyl-1,2-dihydrocyclobutapyrimidine-4,6(3H,5H)-dione (82959-62-4)

Conditions	Yield
In acetone Irradiation;	99%
In acetone at 20℃; for 2h; Cycloaddition; Photolysis;

piperidine (110-89-4) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → 1,3-dimethyl-6-(piperidin-1-yl)pyrimidine-2,4(1H,3H)-dione

Conditions	Yield
at 60℃; for 0.00833333h; microwave irradiation;	99%
In 1,4-dioxane at 100℃; for 2h;	98%
In dichloromethane for 1h; Ambient temperature;	85%
In water Heating;	59%
Stage #1: 1,3-Dimethyl-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: piperidine With triethylamine In N,N-dimethyl-formamide at 23℃; for 2h; Schlenk technique; Inert atmosphere;	168 mg

1,3-Dimethyl-6-chlorouracil (6972-27-6) + sodium methylate (124-41-4) → 6-methoxy-1,3-dimethyluracil (4097-20-5)

Conditions	Yield
In methanol at 60℃; for 0.00833333h; microwave irradiation;	99%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + aniline (62-53-3) → 6-anilino-1,3-dimethyluracil (7278-51-5)

Conditions	Yield
at 160℃; for 0.5h; microwave irradiation;	98%
In neat (no solvent) at 180℃; for 3h;	87%
In ethanol for 12h; Heating;	80%

1,3-Dimethyl-6-chlorouracil (6972-27-6) → 6-chloro-1,3-dimethyl-5-nitrouracil (1203-25-4)

Conditions	Yield
With sulfuric acid; potassium nitrate 1.) 15 min, 7 deg C, 2.) 30 min, 20 deg C;	98%
With sulfuric acid; nitric acid at 5℃;
With nitric acid; sulfuric acid at 10℃; for 2h;

1,3-Dimethyl-6-chlorouracil (6972-27-6) + benzylamine (100-46-9) → 6-(benzylamino)-1,3-dimethyluracil (5770-49-0)

Conditions	Yield
at 130℃; for 0.05h; microwave irradiation;	98%
With triethylamine In 1,4-dioxane for 10h; Reflux;	87%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + sodium ethanolate (141-52-6) → 1,3-dimethyl-6-ethoxyuracil (93787-99-6)

Conditions	Yield
In ethanol at 60℃; for 0.00833333h; microwave irradiation;	97%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + 4-bromo-aniline (106-40-1) → 6-(4-bromo-anilino)-1,3-dimethyl-1H-pyrimidine-2,4-dione (64663-99-6)

Conditions	Yield
In neat (no solvent) at 180℃; for 3h;	97%
at 180℃; for 3h;	70%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + N-butylamine (109-73-9) → 6-n-butylamino-1,3-dimethyluracil (5770-46-7)

Conditions	Yield
In N,N-dimethyl-formamide for 18h; Reflux;	96%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + methylamine (74-89-5) → 1,3-dimethyl-6-methylamino-1H-pyrimidine-2,4-dione (5770-42-3)

Conditions	Yield
In methanol for 16h; Large scale;	95%
With water
In water

N-methylpropargylamine (35161-71-8) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → 1,3-dimethyl-6-(N-methyl-N-propargyl)aminouracil (94154-86-6)

Conditions	Yield
	95%
for 6h; Ambient temperature;	87.7%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + benzyl-methyl-amine (103-67-3) → 1,3-dimethyl-6-(benzylmethylamino)uracil

Conditions	Yield
at 130℃; for 0.0166667h; microwave irradiation;	94%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 1,3-dimethyl-6-phenyluracil (42542-99-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 16h; Suzuki-Miyaura coupling; Reflux;	94%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + sodium thiophenolate (930-69-8) → 1,3-dimethyl-6-phenylthiouracil (35218-98-5)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 60℃; for 0.00833333h; microwave irradiation;	93%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + methyl 2-(11-(3-(piperazin-1-yl)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate (943783-06-0) → methyl 2-(11-(3-(4-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)piperazin-1-yl)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate (943781-13-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 7h;	93%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + 1-(2,4-dichlorophenyl)oxy-4-chloro-but-2-yne (68536-76-5) → 6-[4-(2,4-dichloro-phenoxy)-but-2-ynylsulfanyl]-1,3-dimethyl-1H-pyrimidine-2,4-dione (897935-82-9)

Conditions	Yield
Stage #1: 1,3-Dimethyl-6-chlorouracil With sodium hydrogensulfide In ethanol at 0℃; for 6h; Stage #2: 1-(2,4-dichlorophenyl)oxy-4-chloro-but-2-yne With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water at 20℃; for 12h;	92%

N-(2-bromo-5-methoxybenzyl),N-methylamine (767289-08-7) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → 6-((2-bromo-5-methoxybenzyl)(methyl)amino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (1148107-95-2)

Conditions	Yield
In ethanol Reflux;	92%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + 4-methoxy-aniline (104-94-9) → 6-p-Methoxyphenylamino-1,3-dimethyluracil (58137-44-3)

Conditions	Yield
In neat (no solvent) at 180℃; for 3h;	91%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + 2-chloro-4-iodoaniline (42016-93-3) → C12H11ClIN3O2 (1026989-89-8)

Conditions	Yield
Stage #1: 1,3-Dimethyl-6-chlorouracil; 2-chloro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 5℃; for 0.833333h; Stage #2: With water; ammonium chloride In tetrahydrofuran	91%

1,3-Dimethyl-6-chlorouracil (6972-27-6) + p,p'-diaminobiphenyl (92-87-5) → 6,6'-[biphenyl-4,4'-diyldi(imino)]bis(1,3-dimethylpyrimidine-2,4(1H,3H)-dione) (1448799-77-6)

Conditions	Yield
With quinoline at 180℃; for 3h;	91%

pyrrolidine (123-75-1) + 1,3-Dimethyl-6-chlorouracil (6972-27-6) → N,N-dimethyl-6-pyrrolidino uracil (74151-85-2)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	90%
In ethanol Ambient temperature;

Upstream product

• 74-83-9 methyl bromide 
• 4318-56-3 3-methyl-6-chlorouracil 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 4270-27-3 6-chlorouracil 
• 74-88-4 methyl iodide 
• 89-25-8 edaravone 
• 35824-85-2 6-chloro-5-formyl-1,3-dimethyluracil 
• 769-42-6 1,3-dimethylbarbituric acid 
• 6320-15-6 6-chloro-2,4-dimethoxypyrimidine 

Downstream Products

• 51369-91-6 1,3-dimethyl-6-(3-phenyl-oxiranyl)-1H-pyrimidine-2,4-dione 
• 3120-45-4 3.3.5.7-Tetramethyl-6.8-dioxo-5.6.7.8-tetrahydro-3H-pyrimido<5.4-c>-1.2.5-oxadiazin 
• 253197-17-0 6-(p-Ethoxycarbonylphenylamino)-1,3-dimethyluracil 
• 506437-12-3 N-(1,3-dimethyl-6-uracilyl)-S,S-diphenylsulfilimine 
• 518050-98-1 N-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)phenyl]pivalamide 
• 518050-99-2 N-[4-chloro-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)phenyl]pivalamide 
• 35218-98-5 1,3-dimethyl-6-thiophenyluracil 
• 5770-49-0 6-(benzylamino)-1,3-dimethyluracil 
• 51759-19-4 1,3-dimethyl-6-phenoxyuracil 
• 5770-45-6 1,3-dimethyl-6-propylamino-1H-pyrimidine-2,4-dione 
• 2278-15-1 1,3-Dimethyl-8-azaxanthine 
• 65183-48-4 3,5,7-trimethylisoxazolo<3,4-d>pyrimidine-4,6(5H,7H)-dione 
• 33070-47-2 4,6-dimethyl[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione 
• 65183-49-5 5,7-dimethyl-3-phenylisoxazolo<3,4-d>pyrimidine-4,6(5H,7H)-dione 

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