608-34-4

Basic information

• Product Name: 3-METHYLURACIL
• Synonyms: 3-MeU;NSC 45626;3-Methyl-2,4(1H,3H)-pyrimidinedione;3-Methylpyrimidine-2,4(1H,3H);3-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE;3-METHYLURACIL;TIMTEC-BB SBB004255;2,4(1H,3H)-Pyrimidinedione, 3-methyl-
• CAS NO: 608-34-4
• Molecular Formula: C₅H₆N₂O₂
• Molecular Weight: 126.11
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 608-34-4.mol
• Article Data: 34

Chemical Properties

• Melting Point: 223-226 °C
• Boiling Point: 272.17°C (rough estimate)
• Flash Point: 111.1 °C
• Appearance: /
• Density: 1.4760 (rough estimate)
• Vapor Pressure: 0.00181mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: −20°C
• PKA: 9.95±0.10(Predicted)
• Water Solubility: 200g/L(temperature not stated)
• CAS DataBase Reference: 3-METHYLURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLURACIL(608-34-4)
• EPA Substance Registry System: 3-METHYLURACIL(608-34-4)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 608-34-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A pyrimidone that is uracil with a methyl group at position 3.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 18, p. 339, 1981 DOI: 10.1002/jhet.5570180222Tetrahedron, 39, p. 3919, 1983 DOI: 10.1016/S0040-4020(01)90895-6

InChI:InChI=1/C5H6N2O2/c1-7-4(8)2-3-6-5(7)9/h2-3H,1H3,(H,6,9)

Synthetic route

2-methoxy-3-methylpyrimidin-4(3H)-one (27460-04-4) → 3-methyluracil (608-34-4)

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

5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione (6832-03-7) → 3-methyluracil (608-34-4)

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%

orthoformic acid triethyl ester (122-51-0) + N-Methylurea (598-50-5) + Polymer: 4-phenylbutan-2-one cyclic malonic acid ester, bound to Merrifield resin → 3-methyluracil (608-34-4)

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%

(3-methyl-uracil-4-ylidene)W(CO)5 → 3-methyluracil (608-34-4)

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

3-methyl-2,3-dihydro-2-thioxo-pyrimidin-4(1H)-one (576-28-3) → 3-methylpyrimidin-4-one (6104-45-6) + 3-methyluracil (608-34-4) + SO2, H2SO4

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

3-methyl-5,8-methano-3,4,r-4a,c-5,c-8,c-8a-hexahydroquinazoline-2,4-dione (113094-27-2) → 3-methyluracil (608-34-4)

Conditions	Yield
for 0.166667h; Heating;	65%

3-methylpyrimidin-4-one (6104-45-6) → 3-methyluracil (608-34-4)

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.

1-methylindole (603-76-9) + 5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione (6832-03-7) → 3-methyluracil (608-34-4) + 3-methyl-6-(1-methylindol-3-yl)uracil (89246-31-1) + 3-methyl-5-(1-methylindol-3-yl)uracil (89246-32-2)

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

5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione (6832-03-7) + 1-Benzyl-1,4-dihydronicotinamide (952-92-1) → 3-methyluracil (608-34-4) + 1-benzyl-3-methyl-2,4-pyrimidinedione (61686-79-1) + 5-benzyl-3-methyluracil (61686-78-0)

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%

5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione (6832-03-7) + N,N-dimethyl acetamide (127-19-5) → 3-methyluracil (608-34-4) + 5,5'-methylenebis(3-methyluracil) (81078-01-5)

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

5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione (6832-03-7) → 3-methyluracil (608-34-4) + 5,5'-methylenebis(3-methyluracil) (81078-01-5)

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

2,2-dimethyl-4H-1,3-dioxin-4-one (87769-48-0) + N-Methylurea (598-50-5) → 1-methyluracil (615-77-0) + 3-methyluracil (608-34-4)

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

uracil (66-22-8) + dimethyl sulfate (77-78-1) → 1-methyluracil (615-77-0) + 3-methyluracil (608-34-4) + 1,3-dimethyluracil (874-14-6)

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%

trimethyl phosphite (512-56-1) + Cytosine (71-30-7) → 3-methylcytosine (4776-08-3) + 3-methyluracil (608-34-4) + 1-MeCyt (1122-47-0) + 1,3-dimethylcytosine (6749-87-7)

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

2'-deoxy-3-N-methyl-3',5'-di-O-methyl-2'-methyleneuridine (1174638-88-0) + trimethylsilyl-2,2-difluoro-2-(fluorosulphonyl)acetate (120801-75-4) → 3-methyluracil (608-34-4) + 2-O-difluoromethyl-3-N-methyluracil (1174638-90-4)

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%

2-methylthio-3-methylpyrimidin-4(3H)-one (6327-98-6) → 3-methyluracil (608-34-4)

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

1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid (705-36-2) → 3-methyluracil (608-34-4)

Conditions	Yield
at 310℃;
With quinoline; copper

3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (51727-06-1) → 3-methyluracil (608-34-4)

Conditions	Yield
at 255℃;

1-methyl-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid (101861-31-8) → 3-methyluracil (608-34-4)

Conditions	Yield
With hydrogenchloride

diazomethane (186581-53-3, 908094-01-9) + carbonylphenyluracil (2775-86-2) → 3-methyluracil (608-34-4)

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

3-methyl-5,6-dihydropyrimidine-2,4(1H,3H)-dione (1672-04-4) → 3-methyluracil (608-34-4)

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

5-diazo-6-methoxy-3-methyldihydrouracil (57381-19-8) → 3-methyluracil (608-34-4)

Conditions	Yield
In acetonitrile at 100℃;

3-methylisouracil (95035-32-8) → 3-methyluracil (608-34-4)

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

1,6-dihydro-1-methyl-2-<2-(2-methylpropoxy)anilino>-6-dioxo-5-pyrimidinecarboxylic acid (124769-85-3) → 3-methyluracil (608-34-4) + 2-(2methylpropoxy)aniline hydrochloride (124769-90-0)

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

sulfuric acid (7664-93-9) + 3-methyluridine (2140-69-4) → 3-methyluracil (608-34-4)

Conditions	Yield
at 125℃;

3-methyl-2-ethylsulfanyl-pyrimidone-(4) → 3-methyluracil (608-34-4)

Conditions	Yield
With hydrogenchloride

trans,anti-(1,3-dimethyluracil) dimer (31356-07-7, 32477-76-2) → 3-methyluracil (608-34-4) + 1,3-dimethyluracil (874-14-6) + 1,3-dimethyluracil (4874-13-9) + 1,3,6-trimethyl-1H,6H-pyrido[4,3-d]pyrimidine-2,4,7-trione

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

cis,anti-(1,3-dimethyluracil) dimer → 1-methyluracil (615-77-0) + 3-methyluracil (608-34-4) + 1,3-dimethyluracil (874-14-6) + 1,3-dimethyluracil (4874-13-9)

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

2-ethoxy-3-methylpyrimidin-4-one (20541-38-2) → 3-methyluracil (608-34-4)

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

3-methyluracil (608-34-4) + diphenyl diselenide (1666-13-3) → 3-methyl-5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione

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%

3-methyluracil (608-34-4) + para-thiocresol (106-45-6) → 3-methyl-5-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione

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%

3-methyluracil (608-34-4) + diethyl sulfate (64-67-5) → 1-ethyl-3-methyl-2,4-pyrimidinedione

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

3-methyluracil (608-34-4) + benzyl tosylate (1024-41-5) → 1-benzyl-3-methyl-2,4-pyrimidinedione (61686-79-1)

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

3-methyluracil (608-34-4) + Hexyl isocyanate (2525-62-4) → N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide (1431627-93-8)

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℃;

3-methyluracil (608-34-4) + ethylene dibromide (106-93-4) → 1-(2-bromoethyl)-3-methylpyrimidine-2,4(1H,3H)-dione

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

3-methyluracil (608-34-4) + (1R,2R)-2-aminocyclopentan-1-ol hydrochloride (68327-11-7) → 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one (1228684-00-1)

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%

3-methyluracil (608-34-4) + 3-chloro-4-fluoronitrobenzene (350-30-1) → 1-(2-chloro-4-nitrophenyl)-3-methyl-1H-pyrimidine-2,4-dione (1533425-47-6)

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

3-methyluracil (608-34-4) + formaldehyd (50-00-0) → 5-(chloromethyl)-3-methyluracil (32079-00-8)

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

3-methyluracil (608-34-4) → 1-formyl-5-hydroxy-3-methylhydantoin (124443-47-6)

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%

3-methyluracil (608-34-4) + 1,10-diiododecane (16355-92-3) → 1,1'-(1,10-decanediyl)bis<3-methyluracil>

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

3-methyluracil (608-34-4) + 1,6-diiodohexane (629-09-4) → 1,1'-(1,6-hexanediyl)bis<3-methyluracil>

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

3-methyluracil (608-34-4) → 1-formyl-5-hydroxy-3-methylhydantoin (124443-47-6) + 3-methyl-5-hydroxy-imidazoline-2,4-dione (100558-37-0)

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

1,4-Diiodobutane (628-21-7) + 3-methyluracil (608-34-4) → 1,4-bis(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)butane

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

3-methyluracil (608-34-4) + 1,8-diiodooctane (24772-63-2) → 1,1'-(1,8-octanediyl)bis<3-methyluracil>

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

3-methyluracil (608-34-4) + 1,12-dibromododecane (3344-70-5) → 1,1'-(1,12-dodecanediyl)bis<3-methyluracil>

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

3-methyluracil (608-34-4) + diiodomethane (75-11-6) → bis(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)methane

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

3-methyluracil (608-34-4) + 1,3-Diiodopropane (627-31-6) → 1,3-bis(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)propane

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

Upstream product

• 6327-98-6 2-methylthio-3-methylpyrimidin-4(3H)-one 
• 705-36-2 1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid 
• 51727-06-1 3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid 
• 603-76-9 1-methylindole 
• 6832-03-7 5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione 
• 512-56-1 trimethyl phosphite 
• 71-30-7 Cytosine 
• 95035-32-8 3-methylisouracil 
• 7664-93-9 sulfuric acid 
• 2140-69-4 3-methyluridine 
• 576-28-3 3-methyl-2,3-dihydro-2-thioxo-pyrimidin-4(1H)-one 
• 66-22-8 uracil 
• 77-78-1 dimethyl sulfate 
• 103860-72-6 ethyl 1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate 

Downstream Products

• 66819-95-2 3-Methyl-2,4-dithiouracil 
• 79719-30-5 1-hydroxymethyl-3-methyluracil 
• 115923-81-4 Acetic acid 5,5-difluoro-1-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 115923-75-6 Acetic acid (4S,5R)-5-fluoro-1-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 115923-75-6 Acetic acid (4S,5S)-5-fluoro-1-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 4840-69-1 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione 
• 6832-03-7 5-bromo-3-methyl-2,4(1H,3H)pyrimidinedione 
• 25912-37-2 3-methyl-5-nitro-2,4(1H,3H)pyrimidinedione 
• 124443-47-6 1-formyl-5-hydroxy-3-methylhydantoin 
• 100558-37-0 3-methyl-5-hydroxy-imidazoline-2,4-dione 
• 115923-78-9 (5R,6S)-5-Fluoro-6-hydroxy-3-methyl-dihydro-pyrimidine-2,4-dione 
• 115923-78-9 (5R,6R)-5-Fluoro-6-hydroxy-3-methyl-dihydro-pyrimidine-2,4-dione 
• 61686-79-1 1-benzyl-3-methyl-2,4-pyrimidinedione 

Relevant articles and documents

-

-

Pyrimidinedione derivative capable of inhibiting monocarboxylate transporter

The invention relates to a pyrimidinedione derivative capable of inhibiting a monocarboxylate transporter, the pyrimidinedione derivative is a formula (I) compound and/or a pharmaceutically acceptablesalt thereof, and/or a stereoisomer thereof, and/or a solvate thereof, the compound has the effect of inhibiting the activity of the monocarboxylate transporter, and also comprises a pharmaceutical composition containing the formula (I) compound and the use of the pharmaceutical composition in treatment.

Discovery of a new class of highly potent inhibitors of acid ceramidase: Synthesis and structure-activity relationship (SAR)

Acid ceramidase (AC) is an intracellular cysteine amidase that catalyzes the hydrolysis of the lipid messenger ceramide. By regulating ceramide levels in cells, AC may contribute to the regulation of cancer cell proliferation and senescence and to the response to cancer therapy. We recently identified the antitumoral agent carmofur (4a) as the first nanomolar inhibitor of intracellular AC activity (rat AC, IC50 = 0.029 μM). In the present work, we expanded our initial structure-activity relationship (SAR) studies around 4a by synthesizing and testing a series of 2,4-dioxopyrimidine-1- carboxamides. Our investigations provided a first elucidation of the structural features of uracil derivatives that are critical for AC inhibition and led us to identify the first single-digit nanomolar inhibitors of this enzyme. The present results confirm that substituted 2,4-dioxopyrimidine-1-carboxamides are a novel class of potent inhibitors of AC. Selected compounds of this class may represent useful probes to further characterize the functional roles of AC.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.