2,4(1H,3H)-Pyrimidinedione, 3-methyl- supplier

Name
3-METHYLURACIL
EINECS
CAS No. 608-34-4
Article Data57
CAS DataBase
Density 1.263 g/cm³
Solubility 200g/L(temperature not stated)
Melting Point 223-226 °C
Formula C₅H₆N₂O₂
Boiling Point 260.1 °C at 760 mmHg
Molecular Weight 126.115
Flash Point 111.1 °C
Transport Information
Appearance
Safety 22-36
Risk Codes 40
Molecular Structure
Hazard Symbols Xn
Synonyms Uracil,3-methyl- (7CI,8CI);3-Methyl-2,4(1H,3H)-pyrimidinedione;3-Methyluracil;NSC45626;
PSA 54.86000
LogP -0.92640

Synthetic route

: 27460-04-4
2-methoxy-3-methylpyrimidin-4(3H)-one

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 60℃; for 2h; Hydrolysis;	98%

: 6832-03-7
5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With N-methylphenothiazine at 170℃; for 0.5h;	87%
With sodium dithionite; sodium carbonate In water; acetonitrile for 1h; Ambient temperature;	85.6%
With Me2SiI In acetonitrile at 20℃; for 2h;	7%

: 122-51-0
orthoformic acid triethyl ester

: 598-50-5
N-Methylurea

Polymer: 4-phenylbutan-2-one cyclic malonic acid ester, bound to Merrifield resin: Polymer: 4-phenylbutan-2-one cyclic malonic acid ester, bound to Merrifield resin

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; Polymer: 4-phenylbutan-2-one cyclic malonic acid ester, bound to Merrifield resin for 6h; Heating; Stage #2: N-Methylurea for 12h; Heating; Stage #3: at 220 - 240℃; for 0.333333h; Further stages.;	82%

...Expand

(3-methyl-uracil-4-ylidene)W(CO)5: (3-methyl-uracil-4-ylidene)W(CO)5

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In 1,2-dichloro-ethane at 70℃; for 8h;	80%

: 576-28-3
3-methyl-2,3-dihydro-2-thioxo-pyrimidin-4(1H)-one

A: 6104-45-6
3-methylpyrimidin-4-one

B: 608-34-4
3-methyluracil

C SO2, H2SO4: SO2, H2SO4

Conditions

Conditions	Yield
With oxygen; ozone In acetic acid for 0.1h; Ambient temperature;	A 72% B 25% C n/a

...Expand

: 113094-27-2
3-methyl-5,8-methano-3,4,r-4a,c-5,c-8,c-8a-hexahydroquinazoline-2,4-dione

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
for 0.166667h; Heating;	65%

: 6104-45-6
3-methylpyrimidin-4-one

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With oxygen; aldehyde oxidase In water at 25℃; Kinetics; Mechanism; Product distribution; pH optimum;	64%
Rabbit liver aldehyde oxidase immobilized onto DEAE Sepharose CL 6B at 4℃; 10 mM potassium phosphate buffer, pH 7.5, 0.1 mM EDTA;	64 % Spectr.

: 603-76-9
1-methylindole

: 6832-03-7
5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione

A: 608-34-4
3-methyluracil

B: 89246-31-1
3-methyl-6-(1-methylindol-3-yl)uracil

C: 89246-32-2
3-methyl-5-(1-methylindol-3-yl)uracil

Conditions

Conditions	Yield
at 170℃; for 0.5h;	A 55% B 9% C 18%

...Expand

: 6832-03-7
5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione

: 952-92-1
1-Benzyl-1,4-dihydronicotinamide

A: 608-34-4
3-methyluracil

B: 61686-79-1
1-benzyl-3-methyl-2,4-pyrimidinedione

C: 61686-78-0
5-benzyl-3-methyluracil

Conditions

Conditions	Yield
at 180℃; for 3h; Product distribution; Mechanism; examination of further 5-bromouracils, reducing compounds, solvent, temperature and reaction time;	A 54% B 9.7% C 19.4%
at 180℃; for 3h;	A 54% B 9.7% C 19.4%

...Expand

: 6832-03-7
5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione

: 127-19-5
N,N-dimethyl acetamide

A: 608-34-4
3-methyluracil

B: 81078-01-5
5,5'-methylenebis(3-methyluracil)

Conditions

Conditions	Yield
at 180℃; for 6h;	A 50.4% B 37%

...Expand

: 6832-03-7
5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione

A: 608-34-4
3-methyluracil

B: 81078-01-5
5,5'-methylenebis(3-methyluracil)

Conditions

Conditions	Yield
With N,N-dimethyl acetamide at 180℃; for 6h;	A 50.4% B 37%

: 87769-48-0
2,2-dimethyl-4H-1,3-dioxin-4-one

: 598-50-5
N-Methylurea

A: 615-77-0
1-methyluracil

B: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; toluene for 0.166667h; Heating;	A 39% B 32%

...Expand

: 66-22-8
uracil

: 77-78-1
dimethyl sulfate

A: 615-77-0
1-methyluracil

B: 608-34-4
3-methyluracil

C: 874-14-6
1,3-dimethyluracil

Conditions

Conditions	Yield
Stage #1: uracil With lithium hydride In N,N-dimethyl-formamide at 60℃; for 0.5h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 60℃; for 72h;	A 30% B 5% C 12%

...Expand

: 512-56-1
trimethyl phosphite

: 71-30-7
Cytosine

A: 4776-08-3
3-methylcytosine

B: 608-34-4
3-methyluracil

C: 1122-47-0
1-MeCyt

D: 6749-87-7
1,3-dimethylcytosine

Conditions

Conditions	Yield
In ethanol at 80℃; for 31h;	A 20% B 10% C 4% D 11%

...Expand

: 1174638-88-0
2'-deoxy-3-N-methyl-3',5'-di-O-methyl-2'-methyleneuridine

: 120801-75-4
trimethylsilyl-2,2-difluoro-2-(fluorosulphonyl)acetate

A: 608-34-4
3-methyluracil

B: 1174638-90-4
2-O-difluoromethyl-3-N-methyluracil

Conditions

Conditions	Yield
Stage #1: 2'-deoxy-3-N-methyl-3',5'-di-O-methyl-2'-methyleneuridine With sodium fluoride In toluene at 110℃; for 0.5h; Inert atmosphere; Stage #2: trimethylsilyl-2,2-difluoro-2-(fluorosulphonyl)acetate In toluene Reflux; Inert atmosphere;	A 11% B 17%

...Expand

: 6327-98-6
2-methylthio-3-methylpyrimidin-4(3H)-one

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With hydrogenchloride
With hydrogenchloride
With sodium hydroxide; water at 45 - 70℃; Kinetics;

: 705-36-2
1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
at 310℃;
With quinoline; copper

: 51727-06-1
3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
at 255℃;

: 101861-31-8
1-methyl-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With hydrogenchloride

: 186581-53-3, 908094-01-9
diazomethane

: 2775-86-2
carbonylphenyluracil

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With methylamine 1.) acetone-ether; 2.) ethanol; Yield given. Multistep reaction;

: 1672-04-4
3-methyl-5,6-dihydropyrimidine-2,4(1H,3H)-dione

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With dinitrogen monoxide; potassium hexacyanoferrate(III) In water at 20℃; Irradiation;

: 57381-19-8
5-diazo-6-methoxy-3-methyldihydrouracil

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
In acetonitrile at 100℃;

: 95035-32-8
3-methylisouracil

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With dinitrogen monoxide; potassium hexacyanoferrate(III) In water at 20℃; Rate constant; Irradiation; investigation of rearrangements depending on pH;

: 124769-85-3
1,6-dihydro-1-methyl-2-<2-(2-methylpropoxy)anilino>-6-dioxo-5-pyrimidinecarboxylic acid

A: 608-34-4
3-methyluracil

B: 124769-90-0
2-(2methylpropoxy)aniline hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In acetone for 5h; Product distribution; Heating;

: 7664-93-9
sulfuric acid

: 2140-69-4
3-methyluridine

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
at 125℃;

3-methyl-2-ethylsulfanyl-pyrimidone-(4): 3-methyl-2-ethylsulfanyl-pyrimidone-(4)

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With hydrogenchloride

: 31356-07-7, 32477-76-2
trans,anti-(1,3-dimethyluracil) dimer

A: 608-34-4
3-methyluracil

B: 874-14-6
1,3-dimethyluracil

C: 4874-13-9
1,3-dimethyluracil

D: 1,3,6-trimethyl-1H,6H-pyrido[4,3-d]pyrimidine-2,4,7-trione

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile for 2h; Product distribution; Irradiation;

...Expand

: cis,anti-(1,3-dimethyluracil) dimer

A: 615-77-0
1-methyluracil

B: 608-34-4
3-methyluracil

C: 874-14-6
1,3-dimethyluracil

D: 4874-13-9
1,3-dimethyluracil

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile for 2h; Product distribution; Irradiation;

...Expand

: 20541-38-2
2-ethoxy-3-methylpyrimidin-4-one

: 608-34-4
3-methyluracil

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃; for 20h;	1.65 g

: 608-34-4
3-methyluracil

: 1666-13-3
diphenyl diselenide

: 3-methyl-5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 50℃; for 3h; Schlenk technique;	99%
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 50℃;	92%

: 608-34-4
3-methyluracil

: 106-45-6
para-thiocresol

: 3-methyl-5-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 100℃; for 18h; Schlenk technique;	92%
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 100℃; for 15h;	83%

: 608-34-4
3-methyluracil

: 64-67-5
diethyl sulfate

: 1-ethyl-3-methyl-2,4-pyrimidinedione

Conditions

Conditions	Yield
With lithium hydride In 1,4-dioxane at 60℃; for 24h; Alkylation;	90%

: 608-34-4
3-methyluracil

: 1024-41-5
benzyl tosylate

: 61686-79-1
1-benzyl-3-methyl-2,4-pyrimidinedione

Conditions

Conditions	Yield
With lithium hydride In 1,4-dioxane at 60℃; for 10h; Alkylation;	85%

: 608-34-4
3-methyluracil

: 2525-62-4
Hexyl isocyanate

: 1431627-93-8
N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide

Conditions

Conditions	Yield
Stage #1: 3-methyluracil With pyridine; dmap at 20℃; for 0.5h; Inert atmosphere; Stage #2: Hexyl isocyanate at 20℃; for 12h; Inert atmosphere;	79%
With pyridine; dmap; triethylamine In toluene at 90℃; for 3h;
With pyridine; dmap at 60℃;

: 608-34-4
3-methyluracil

: 106-93-4
ethylene dibromide

: 1-(2-bromoethyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;	77%

: 608-34-4
3-methyluracil

: 68327-11-7
(1R,2R)-2-aminocyclopentan-1-ol hydrochloride

: 1228684-00-1
2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 3-methyluracil With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 18 - 25℃; for 0.0333333h; Stage #2: (1R,2R)-2-aminocyclopentan-1-ol hydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 18 - 25℃;	76%
Stage #1: 3-methyluracil With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: (1R,2R)-2-aminocyclopentan-1-ol hydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃;	76%

: 608-34-4
3-methyluracil

: 350-30-1
3-chloro-4-fluoronitrobenzene

: 1533425-47-6
1-(2-chloro-4-nitrophenyl)-3-methyl-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; Inert atmosphere;	71%

: 608-34-4
3-methyluracil

: 50-00-0
formaldehyd

: 32079-00-8
5-(chloromethyl)-3-methyluracil

Conditions

Conditions	Yield
With hydrogenchloride for 0.333333h; Heating;	68%

: 608-34-4
3-methyluracil

: 124443-47-6
1-formyl-5-hydroxy-3-methylhydantoin

Conditions

Conditions	Yield
With oxygen; ozone In acetic acid at 20℃; for 0.333333h; Product distribution;	59%
With oxygen; ozone In acetic acid at 20℃; for 0.333333h;	59%

: 608-34-4
3-methyluracil

: 16355-92-3
1,10-diiododecane

: 1,1'-(1,10-decanediyl)bis<3-methyluracil>

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 20h;	56%

: 608-34-4
3-methyluracil

: 629-09-4
1,6-diiodohexane

: 1,1'-(1,6-hexanediyl)bis<3-methyluracil>

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 20h;	48%

: 608-34-4
3-methyluracil

A: 124443-47-6
1-formyl-5-hydroxy-3-methylhydantoin

B: 100558-37-0
3-methyl-5-hydroxy-imidazoline-2,4-dione

Conditions

Conditions	Yield
With oxygen; ozone In water at 37℃; for 2h;	A 44% B 9%

: 628-21-7
1,4-Diiodobutane

: 608-34-4
3-methyluracil

: 1,4-bis(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)butane

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 20h;	43%

: 608-34-4
3-methyluracil

: 24772-63-2
1,8-diiodooctane

: 1,1'-(1,8-octanediyl)bis<3-methyluracil>

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 20h;	43%

: 608-34-4
3-methyluracil

: 3344-70-5
1,12-dibromododecane

: 1,1'-(1,12-dodecanediyl)bis<3-methyluracil>

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 20h;	42%

: 608-34-4
3-methyluracil

: 75-11-6
diiodomethane

: bis(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)methane

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 20h;	40%

: 608-34-4
3-methyluracil

: 627-31-6
1,3-Diiodopropane

: 1,3-bis(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)propane

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 20h;	35%

2,4(1H,3H)-Pyrimidinedione, 3-methyl- Specification

This chemical is called 2,4(1H,3H)-Pyrimidinedione, 3-methyl-, and it can also be named as 3-Methyluracil. With the molecular formula of C₅H₆N₂O₂, its product categories are Biochemicals and Reagents; Nucleoside Analogs; Nucleosides, Nucleotides, Oligonucleotides. The CAS registry number of this chemical is 608-34-4. Additionally, it should be stored at -20°C.

Other characteristics of the 2,4(1H,3H)-Pyrimidinedione, 3-methyl- can be summarised as followings: (1)ACD/LogP: -0.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.25; (4)ACD/LogD (pH 7.4): -0.26; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 17.35; (8)ACD/KOC (pH 7.4): 17.17; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 40.62 Å²; (13)Index of Refraction: 1.511; (14)Molar Refractivity: 29.93 cm³; (15)Molar Volume: 99.8 cm³; (16)Polarizability: 11.86×10^-24cm³; (17)Surface Tension: 41.3 dyne/cm; (18)Density: 1.263 g/cm³; (19)Flash Point: 111.1 °C; (20)Enthalpy of Vaporization: 57.82 kJ/mol; (21)Boiling Point: 260.1 °C at 760 mmHg; (22)Vapour Pressure: 0.00181 mmHg at 25°C.

Production method of this chemical: The 2,4(1H,3H)-Pyrimidinedione, 3-methyl- could be obtained by the reactant of 3-methyl-3H-pyrimidin-4-one. This reaction needs the catalyts of Rabbit liver aldehyde oxidase immobilized onto DEAE Sepharose CL 6B. The yield is 64 %. In addition, this reaction should be taken at 4 °C.

Uses of this chemical: The 2,4(1H,3H)-Pyrimidinedione, 3-methyl- could react with 1,4-diiodo-butane, and obtain the 1,1'-tetramethylenebis(3-methyluracil). This reaction needs the reagent of NaH, and the solvent of dimethylformamide. The yield is 43 %. In addition, this reaction should be taken for 20 hours at 20-80 °C.

When you are using this chemical, please be cautious about it as the following: This chemical has limited evidence of a carcinogenic effect. Do not breathe dust. Wear suitable protective clothing.

You can still convert the following datas into molecular structure:
1.SMILES: O=C1\C=C/NC(=O)N1C
2.InChI: InChI=1/C5H6N2O2/c1-7-4(8)2-3-6-5(7)9/h2-3H,1H3,(H,6,9)
3.InChIKey: VPLZGVOSFFCKFC-UHFFFAOYAH

Product Name

3-METHYLURACIL

Synthetic route

2,4(1H,3H)-Pyrimidinedione, 3-methyl- Specification

Related Products

Hot Products