504-17-6

Basic information

• Product Name: 4,6-Dihydroxy-2-mercaptopyrimidine
• Synonyms: TBA;TIMTEC-BB SBB004132;THIOBARBITURIC ACID;2-mercaptobarbituricacid;2-thio-barbituricaci;5h)-pyrimidinedione,dihydro-2-thioxo-6(1h;6(1H,5H)-Pyrimidinedione,dihydro-2-thioxo-4;austranal
• CAS NO: 504-17-6
• Molecular Formula: C₄H₄N₂O₂S
• Molecular Weight: 144.15
• EINECS: 207-985-8
• Product Categories: PYRIMIDINE;Heterocyclic Compounds;Aromatics Compounds;Aromatics;Bases & Related Reagents;Nucleotides;Sulfur & Selenium Compounds;Building Blocks;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks;Pyrimidines;Heterocycle-Pyrimidine series
• Mol File: 504-17-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 245 °C (dec.)(lit.)
• Boiling Point: 463.4 °C at 760 mmHg
• Flash Point: 234 °C
• Appearance: Clear colorless/Liquid
• Density: 1.451 (estimate)
• Refractive Index: 1.7690 (estimate)
• Storage Temp.: Controlled Substance, -20°C Freezer
• Solubility: 50g/l slightly soluble
• PKA: 3.96±0.20(Predicted)
• Water Solubility: <6 g/L (20℃)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 120663
• CAS DataBase Reference: 4,6-Dihydroxy-2-mercaptopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dihydroxy-2-mercaptopyrimidine(504-17-6)
• EPA Substance Registry System: 4,6-Dihydroxy-2-mercaptopyrimidine(504-17-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• RIDADR: UN 3335
• WGK Germany: 2
• RTECS: CQ7700000
• F: 13-23
• TSCA: Yes
• Hazardous Substances Data: 504-17-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Yellow Powder. soluble in hot water, alcohol, ether, alkali and sodium carbonate solution, slightly soluble in water.

Uses

Different sources of media describe the Uses of 504-17-6 differently. You can refer to the following data:
1. 4,6-Dihydroxy-2-mercaptopyrimidine can be used to quantitate lipopolysaccharides, carrageenan, and sialic acids, and to detect lipid hydroperoxides and lipid oxidation.
2. 2-Thiobarbituric acid has been used to measure malondialdehyde (MDA) in lipid peroxidation assay.

Preparation

2-thiobarbituric acid was synthesized by the reaction of diethyl malonate with thiourea. Dissolve thiourea in methanol, add sodium methoxide and diethyl malonate, heat under reflux for 4-5h, then distill under reduced pressure to recover methanol to the end, and add hydrochloric acid to acidify to pH 1-2 after cooling. After standing overnight, thiobarbituric acid crystals were precipitated, filtered, and recrystallized with water to obtain the pure product.

Definition

ChEBI: 2-thiobarbituric acid is a barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur. It has a role as a reagent and an allergen.

General Description

2-Thiobarbituric acid is a molecule made up of heteroatoms: nitrogen, sulphur and oxygen.

Biochem/physiol Actions

2-Thiobarbituric acid (TBA) is useful to quantitate lipopolysaccharides, carrageenan, and sialic acids. It is also used to detect lipid hydroperoxides and lipid oxidation. It has applications in the field of medicine and biochemistry. TBA may possess the ability to prevent metal corrosion.

Purification Methods

Crystallise it from water. [Beilstein 24 H 476, 24 I 414, 24 II 275, 24 III/IV 1884.]

InChI:InChI=1/C4H4N2O2S/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)

Synthetic route

thiourea (17356-08-0) + diethyl malonate (105-53-3) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

Conditions	Yield
With sodium In ethanol for 6h; Reflux;	80%
With ethanol; sodium In neat liquid at 60℃; for 0.5h; Reagent/catalyst; Sonication;	79%
With sodium methylate In methanol at 65℃; for 8h;	72%

Propargylic aldehyde (624-67-9) + 5-Iodo-2'-deoxyuridine (54-42-2) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 3-(5'-Iodo-2'-deoxyuridin-3'-yl)prop-2-enal

Conditions	Yield
With triethylamine In N-methyl-acetamide; ethyl acetate	A n/a B 25%

sodium diethylmalonate (996-82-7, 34727-00-9, 73177-21-6) + thiourea (17356-08-0) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

Conditions	Yield
With ethanol at 80℃;

thiourea (17356-08-0) + malonic acid dimethyl ester (108-59-8) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

Conditions	Yield
In dimethylsulfoxide-d6 at 22 - 28℃; Mechanism; pH = 1-2;

6-Amino-2-thiouracil (1004-40-6) + sulfuric acid (7664-93-9) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

4,6-diaminopyrimidine-2(1H)-thione (1004-39-3) + sulfuric acid (7664-93-9) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

2-thio-barbituric acid diimide-(4.6) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

Conditions	Yield
With sulfuric acid

2-thiobarbituric acid imide-(4) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

Conditions	Yield
With sulfuric acid

sodium diethylmalonate (996-82-7) + thiourea (17356-08-0) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6)

Conditions	Yield
In water

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + N-(3, 5-dichlorophenyl)-2-(4-formylphenoxy)acetamide (575499-16-0) → N-(3,5-dichlorophenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide (1310561-77-3)

Conditions	Yield
In ethanol; water at 80℃;	99.1%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + benzaldehyde (100-52-7) → 5-benzylidene-2-thio-barbituric acid (27470-61-7)

Conditions	Yield
With triethylamine In ethanol for 0.25h; Reflux;	99%
With ethylammonium nitrate at 20℃; for 0.5h; Knoevenagel condensation;	94%
In water at 20℃; for 1h; Knoevenagel condensation;	93%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + p-benzyloxybenzaldehyde (4397-53-9) → 5-(4-(benzyloxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (143034-05-3)

Conditions	Yield
With morpholine In acetic acid; benzene for 15h; Heating;	99%
In ethanol; water at 80℃; for 2h;	98.1%
In ethanol; water at 80℃; for 2h;	98.1%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + DL-2-<(Diethylamino)thioxomethylthio>propionsaeure (53278-43-6) → 5-<2-(Diethylamino)-5-methyl-1,3-dithiol-4-ylio>hexahydro-4,6-dioxo-2-thioxo-5-pyrimidinid (100515-84-2)

Conditions	Yield
With sodium acetate In acetic anhydride at 90℃;	99%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 1-naphthaldehyde (66-77-3) → 5-(1-naphthylidene)-2-thiobarbituric acid (143034-06-4)

Conditions	Yield
With morpholine In acetic acid; benzene for 15h; Heating;	99%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4-nitrobenzaldehdye (555-16-8) → C15H11N5O6S2

Conditions	Yield
In ethanol at 20℃; for 0.5h; Condensation;	99%
In water at 25℃; for 0.333333h;

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + N-(4-acetylphenyl)-2-(4-formylphenoxy)acetamide (331962-59-5) → N-(4-acetylphenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide (1310561-74-0)

Conditions	Yield
In ethanol; water at 80℃;	99%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + orthoformic acid triethyl ester (122-51-0) + sulfamethoxazole (1829-84-1) → 4-{[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}-N-(4-methylisoxazol-3-yl)benzenesulfonamide (1345551-62-3)

Conditions	Yield
In iso-butanol for 3h; Reflux;	99%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4-nitrobenzaldehdye (555-16-8) → 5-(4-nitrophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine 4,6(1H,5H)-dione (1219456-24-2)

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.166667h; Sonication; Green chemistry;	99%
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.133333h; Irradiation; Green chemistry;	98%
With ammonium acetate In neat (no solvent) at 110℃; for 0.0833333h;	91%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4-chlorobenzaldehyde (104-88-1) → 5-(4-chlorophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Catalytic behavior; Solvent; Hantzsch Dihydropyridine Synthesis; Green chemistry;	99%
With copper(II) ferrite; ammonium acetate In water for 0.0666667h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.0833333h; Catalytic behavior; Solvent; Irradiation; Green chemistry;	98%
With ammonium acetate In neat (no solvent) at 110℃; for 0.0833333h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	90%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + C13H16N2O4 → 2',4'-dimethyl-8'-nitro-2-thioxo-1',2,2',3,4',4a'-hexahydro-4H,6'H-spiro[pyrimidine-5,5'-[1,4]oxazino[4,3-a]quinoline]-4,6(1H)-dione

Conditions	Yield
With morpholine In ethanol at 80℃; for 36h; Knoevenagel Condensation; Green chemistry;	99%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + p-formylphenyl p-bromophenylcarbamoylmethyl ether (88951-64-8) → N-(4-bromophenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide (358980-92-4)

Conditions	Yield
In ethanol; water at 80℃;	98.9%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 2-amino-phenol (95-55-6) → 6-(2-hydroxyphenylimine)-2-thioxotetrahydropyrimidin-4(1H)-one

Conditions	Yield
With acetic acid In ethanol for 8h; Reflux;	98.8%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 2-(4-methylpiperazin-1-yl)benzaldehyde (85803-62-9) → C16H18N4O2S

Conditions	Yield
In isopropyl alcohol for 8h; Knoevenagel Condensation; Reflux;	98.7%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + piperonal (120-57-0) → 5-(benzo[d][1,3]dioxol-5-ylmethylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (74051-76-6)

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.166667h; Knoevenagel condensation;	98%
for 0.0333333h; Irradiation;	96%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 2h;	94.2%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4-methoxy-benzaldehyde (123-11-5) → 5-(4-methoxybenzylidene)-2-thiobarbituric acid (60045-61-6)

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.166667h; Knoevenagel condensation;	98%
With morpholine In acetic acid; benzene for 15h; Heating;	97%
With triethylamine In ethanol for 0.25h; Reflux;	97%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + vanillin (121-33-5) → 5-(3-methoxyl-4-hydroxybenzylidene)-2-thioxodihyropyrimidine-4,6(1H,5H)-dione (73681-14-8)

Conditions	Yield
In ethanol; water at 80℃; Knoevenagel condensation;	98%
In ethanol at 80℃; for 2h; Knoevenagel Condensation;	74%
With hydrogenchloride

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4-dimethylamino-benzaldehyde (100-10-7) → 5-[4-(N,N-dimethylamino)benzylidene]-2-thiobarbituric acid (27430-15-5)

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.166667h; Knoevenagel condensation;	98%
In water for 1h; Heating;	96%
In ethanol at 20 - 60℃;	95%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) → BARBITURIC ACID (67-52-7)

Conditions	Yield
With quinolinium monofluorochromate(VI) In acetonitrile for 1.5h; Heating;	98%
With bismuth(III) nitrate In acetonitrile for 0.25h; Heating;	94%
With 2,2'-bipyridinium chlorochromate In acetonitrile for 0.0333333h; Product distribution; Further Variations:; Reagents; Temperatures; without microwave irradiation; solvent-free; microwave irradiation;	93%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-diazonium nitrate → 5-{(4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)hydrazono}-2-thioxopyrimidine-4,6(1H,3H,5H)-dione

Conditions	Yield
With trimethylamine at 20℃; under 375.03 Torr; for 12h;	98%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 3-phenyl-propenal (104-55-2) → 5-(3-Phenyl-allylidene)-2-thioxo-dihydro-pyrimidine-4,6-dione

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.333333h; Knoevenagel condensation;	98%
With 1-butyl-3-methylimidazolium Tetrafluoroborate microwave irradiation;	96.1%
With PVP-Ni nanoparticle In ethylene glycol at 50℃; Knoevenagel condensation;	85%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + benzaldehyde (100-52-7) → 5-phenyl-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.333333h; Reagent/catalyst; Temperature; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.166667h; Sonication; Green chemistry;	95%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 2-(2,4-dichlorobenzylideneamino)naphthalene (85378-39-8) → 3-(2,4-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydrobenzo[f]quinolin-3-carbonyl thiourea

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 100℃; for 6h;	98%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 5-Aminouracil (932-52-5) + 4-fluorobenzaldehyde (459-57-4) → 10-(4-fluorophenyl)-1,3,6,8-tetrahydro-7-thioxo-pyrido[3,2-d:6,5-d']dipyrimidine-2,4,9-trione (1210058-14-2)

Conditions	Yield
In N,N-dimethyl-formamide Microwave irradiation;	98%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4,4'-(butylazanediyl)dibenzaldehyde (207129-05-3) → 5,5'-(4,4'-(hexylazanediyl)bis(4,1-phenylene)bis(methyliden-1-yl))bis(2-thioxopyrimidine-4,6(1H,3H)-dione) (1417732-28-5)

Conditions	Yield
With deep eutectic solvent at 40 - 45℃; for 1h; Knoevenagel Condensation;	98%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 2-nitro-benzaldehyde (552-89-6) → 5-(2-nitrophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.633333h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	95%
With copper(II) ferrite; ammonium acetate In water for 0.0333333h; Microwave irradiation;	95%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.166667h; Irradiation; Green chemistry;	95%
With ammonium acetate In neat (no solvent) at 110℃; for 0.166667h;	88%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 3-methoxy-benzaldehyde (591-31-1) → 5-(3-methoxyphenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.133333h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.5h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.133333h; Irradiation; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.0333333h; Microwave irradiation;	95%
With ammonium acetate In neat (no solvent) at 110℃; for 0.166667h;	90%

pyridine-2-carbaldehyde (1121-60-4) + 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) → 5-(pyridin-2-yl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.0333333h; Microwave irradiation;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.133333h; Irradiation; Green chemistry;	96%
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	95%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	95%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 5-(4-chloro-3-nitrophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	97%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.166667h; Irradiation; Green chemistry;	95%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + C16H11N5O3S2 → 5,5′-(1,4-phenylene)bis(2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d']dipyrimidine-4,6(1H,5H)-dione)

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.333333h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	95%

Upstream product

• 1004-40-6 6-Amino-2-thiouracil 
• 7664-93-9 sulfuric acid 
• 1004-39-3 4,6-diaminopyrimidine-2(1H)-thione 
• 624-67-9 Propargylic aldehyde 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 996-82-7 sodium diethylmalonate 
• 17356-08-0 thiourea 
• 105-53-3 diethyl malonate 
• 108-59-8 malonic acid dimethyl ester 
• 996-82-7 sodium diethylmalonate 

Downstream Products

• 101575-67-1 5-(2-β-D-glucopyranosyloxy-benzylidene)-2-thio-barbituric acid 
• 27430-18-8 5-(furan-2'-ylmethylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 
• 102031-03-8 5-(2-phenyl-chromen-4-ylidene)-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 41334-28-5 4-[(4,6-dioxo-2-thioxo-tetrahydro-pyrimidin-5-ylidene)-hydrazino]-N-thiazol-2-yl-benzenesulfonamide 
• 41334-30-9 4-[(4,6-dioxo-2-thioxo-tetrahydro-pyrimidin-5-ylidene)-hydrazino]-N-(4-methyl-thiazol-2-yl)-benzenesulfonamide 
• 100088-98-0 5-(7-acetoxy-2-phenyl-chromen-4-ylidene)-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 41334-32-1 4-[(4,6-dioxo-2-thioxo-tetrahydro-pyrimidin-5-ylidene)-hydrazino]-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide 
• 101636-03-7 5-(7-benzoyloxy-2-phenyl-chromen-4-ylidene)-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 37042-05-0 5-(4-oxo-2-phenyl-4H-chromen-3-ylmethylene)-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 60921-09-7 5-(2-phenyl-naphtho[1,8-bc]thiophen-5-ylidene)-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 120244-32-8 5-(2-thienylmethylene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione 
• 118965-08-5 5-(3,3-bis(4-(dimethylamino)phenyl)allylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 
• 221619-36-9 5-(1,3-Diphenyl-1H-pyrazol-4-ylmethylene)-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 27430-13-3 5-[(4'-chlorophenyl)methylidene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 

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Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (～30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, 1H-NMR techniques, and the obtained data were also checked from the previously published studies.

Synthesis, spectroscopic characterization, computational exploration of 6-(2-(2, 4-dinitrophenylhydrazano)-tetrahydro-2-thioxopyrimidin-4(1h)-one

The structural and vibrational properties of 6-(2-(2,4-dinitrophenylhydrazano)-tetrahydro-2-thioxopyrimidin-4(1H)-one (3) prepared by condensation of synthesized thiobarbituric acid (1) with 2,4-dinitrophenylhydrazine (2) were studied using experimental F

Synthesis, characterization, solvatochromic properties, and antimicrobial evaluation of 5-acetyl-2-thioxo-dihydro-pyrimidine-4,6-dione-based chalcones

A new series of chalcone analogs namely 5-(3-phenyl-acryloyl)-2-thioxo- dihydro-pyrimidine-4,6-dione have been synthesized from the key intermediate 5-acetyl-2-thioxo-dihydro-pyrimidine-4,6-dione 4′ with different aldehyde derivatives were performed to get the target compounds as thiobarbituric acid-based chalcones 5(a′-k′) and they were obtained in excellent yields. The newly synthesized compounds were characterized by spectral analysis (FT-IR, 1H NMR, 13C NMR, and UV spectroscopy) and elemental analysis. The synthesized compounds were evaluated for their antimicrobial activity against five bacterial strains (S. aureus, S. pyogenes, E. coli, K. pneumoniae, and P. aeruginosa) and four fungal strains (C. albicans, A. clavatus, T. rubrum, and Penicillium wild strain). Among the screened compounds, 5e′ and f′ showed comparable activity (minimum inhibitory concentration = 500 μg/mL) nearly to that of standard antibiotics griseofulvin.