36082-50-5

Basic information

• Product Name: 5-Bromo-2,4-dichloropyrimidine
• Synonyms: BUTTPARK 48\06-22;5-BROMO-2,4-DICHLOROPYRIMIDINE;2,4-DICHLORO-5-BROMO PYRIMIDINE;TIMTEC-BB SBB003301;5-Bromo-2,4-Dichloropyridimidine;5-BROMO-2,4-DICHLOROPYRIMIDINE 99%;5-Bromo-2,4-dichloropyrimidine ,97%;5-Bromo-2,4-dichloropyrimidine,98%
• CAS NO: 36082-50-5
• Molecular Formula: C₄HBrCl₂N₂
• Molecular Weight: 227.87414
• EINECS: -0
• Product Categories: Pyrimidine Series;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Halides;Pyrazines, Pyrimidines & Pyridazines;Pyrimidine;Halogenated;Organohalides;Nucleotides and Nucleosides;Aromatics Compounds;Bases & Related Reagents;Nucleotides;Aromatics;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Building Blocks;C4 to C5;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series
• Mol File: 36082-50-5.mol

Chemical Properties

• Melting Point: 29-30 °C(lit.)
• Boiling Point: 128 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow/Liquid or Low Melting Solid
• Density: 1.781 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: n20/D 1.603(lit.)
• Storage Temp.: Keep Cold
• Solubility: Chloroform (Slightly), Ether (Slightly), Ethyl Acetate (Slightly), Toluene (Slig
• PKA: -4.26±0.29(Predicted)
• BRN: 124441
• CAS DataBase Reference: 5-Bromo-2,4-dichloropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2,4-dichloropyrimidine(36082-50-5)
• EPA Substance Registry System: 5-Bromo-2,4-dichloropyrimidine(36082-50-5)

Safety Data

• Hazard Codes: T,C
• Statements: 23/24/25-34-43
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3263 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 36082-50-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Different sources of media describe the Uses of 36082-50-5 differently. You can refer to the following data:
1. Starting material for the synthesis of trisubstituted pyrimidines via a combination of nucleophilic substitution and palladium-catalyzed aryl cross-coupling.1
2. 5-Bromo-2,4-dichloropyrimidine may be employed as starting reagent for the synthesis of positive allosteric modulators for GABAB receptors (drug-like class of compounds) and pyridinepyrimidine analogs.

General Description

5-Bromo-2,4-dichloropyrimidine is a halogenoprimidine. It has been reported as an intermediate during the synthesis of 2,4-di-t-butoxy-5-bromopyrimidine and 2,4-di-t-butoxy-5-pyrimidineboronic acid.

InChI:InChI=1/C4HBrCl2N2/c5-2-1-8-4(7)9-3(2)6/h1H

Synthetic route

5-bromouracil (51-20-7) → 2,4-dichloro-5-bromopyrimidine (36082-50-5)

Conditions	Yield
With phosphorus pentachloride In 1,1,2-trichloroethane Reagent/catalyst; Solvent; Reflux;	99.5%
With N,N-dimethyl-aniline; trichlorophosphate at 120 - 130℃; for 1.33333h;	96.6%
With phosgene; Tributylphosphine oxide at -5 - 125℃; for 1.83333h; Inert atmosphere;	89.7%

2,4-dihydroxy-5-bromopyrimidine (51-20-7) → 2,4-dichloro-5-bromopyrimidine (36082-50-5)

Conditions	Yield
With pyridine; trichlorophosphate at 160℃; for 2h; Autoclave; neat (no solvent);	91%
With dmap; thionyl chloride; bis(trichloromethyl) carbonate for 12.5h; Reflux; Green chemistry;	90%
With phosphorus pentachloride; trichlorophosphate

5-bromouracil (51-20-7) + phosphorus pentachloride (10026-13-8, 874483-75-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → 2,4-dichloro-5-bromopyrimidine (36082-50-5)

5-bromo-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (113138-12-8) → 2,4-dichloro-5-bromopyrimidine (36082-50-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 90℃;

2,4-dichloro-5-bromopyrimidine (36082-50-5) → 4-amino-5-bromo-2-chloropyrimidine (205672-25-9)

Conditions	Yield
With ammonia In methanol at 20℃;	100%
With ammonium hydroxide In tetrahydrofuran at 20℃; for 12h;	100%
With ammonium hydroxide In tetrahydrofuran; water at 20℃; for 1.5h;	100%

2,4-dichloro-5-bromopyrimidine (36082-50-5) → 5-bromo-2-chloro-pyrimidin-4(3H)-one (844843-37-4)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 6h; Cooling;	86%
Stage #1: 2,4-dichloro-5-bromopyrimidine With sodium hydroxide In tetrahydrofuran at 20℃; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran	64%
Stage #1: 2,4-dichloro-5-bromopyrimidine With sodium hydroxide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;	64%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + (2-aminophenyl)dimethyl phosphorus oxide (1197953-47-1) → (2-((5-bromo-2-chloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide (1407520-11-9)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In N,N-dimethyl-formamide at 65℃; for 8h;	72%
With potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 65℃; for 7h;	66%
With tetrabutylammonium hydrogensulfate; potassium carbonate In N,N-dimethyl-formamide at 65℃; for 7h;	66%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h;	2.96 g

2,4-dichloro-5-bromopyrimidine (36082-50-5) + N-Boc-1,3-diaminopropane (75178-96-0) → (3-((5-bromo-2-chloropyrimidin-4-yl)amino)propyl)carbamic acid tert-butyl ester (1046784-89-7)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 3.5h;	100%
With triethylamine In acetonitrile at 20℃; for 0.5h;	41%
With triethylamine In acetonitrile at 0 - 20℃;
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol regioselective reaction;
With potassium carbonate In isopropyl alcohol at 80℃; for 24h;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + (3-aminophenyl)carbamic acid tert-butyl ester (68621-88-5) → tert-butyl (3-((5-bromo-2-chloropyrimidin-4-yl)amino)phenyl)carbamate (1202760-30-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	99%
With potassium carbonate In N,N-dimethyl-formamide at 21℃; for 16h; Inert atmosphere;	98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	98%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + methylamine (74-89-5) → 5-bromo-2-chloro-N-methyl-pyrimidin-4-amine (205672-24-8)

Conditions	Yield
In methanol at 0 - 20℃; for 3.66667h;	100%
In methanol; water Cooling with ice;	88%
In methanol; ethanol at 0 - 20℃; for 3h;	88%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) → tert-butyl 4-((5-bromo-2-chloropyrimidin-4-yl)amino)piperidine-1-carboxylate (954221-10-4)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 0.5h;	82%
With trimethylamine In acetonitrile at 20℃; for 2h;	82%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃;	67%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + benzyl alcohol (100-51-6) → 2,4-bis(benzyloxy)-5-bromopyrimidine (41244-53-5)

Conditions	Yield
With sodium hydride In toluene at 20 - 25℃; for 12h;	93%
With sodium hydride In toluene at 20℃; for 18h;	91%
With sodium hydride 1.) toluene, 50 deg C, 2.) toluene, 25 deg C, overnight; Yield given. Multistep reaction;
With sodium hydride

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 4-Aminobutanol (13325-10-5) → 4-((5-bromo-2-chloropyrimidin-4-yl)amino)butan-1-ol (477593-33-2)

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 16h;	98%
With triethylamine In acetonitrile at 0 - 20℃; for 16h;	98%
With triethylamine In butan-1-ol at 125℃; for 1h; Inert atmosphere; Microwave irradiation;	77%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 0.333333h; Microwave irradiation;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + (3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine (147081-44-5) → (S)-tert-butyl 3-(5-bromo-2-chloropyrimidin-4-ylamino)pyrrolidine-1-carboxylate (1146159-74-1)

Conditions	Yield
With triethylamine In 1,4-dioxane at 10 - 20℃; for 20h;	67%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In acetonitrile at 0 - 20℃;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;
With potassium carbonate In acetonitrile at 20℃;

2,4-dichloro-5-bromopyrimidine (36082-50-5) → 1-(5-bromo-2-chloropyrimidine-4-yl)hydrazine (1021268-16-5)

Conditions	Yield
With hydrazine hydrate In ethanol for 12h; Reflux; Inert atmosphere;	100%
With hydrazine hydrate In methanol at 20℃; for 1h; Cooling with ice;	87%
With hydrazine hydrate In ethanol at 5 - 20℃; for 1h;	75%
With hydrazine hydrate; triethylamine In ethanol at 20℃; for 1h; Cooling with ice;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + cyclohexylamine (108-91-8) → 5-bromo-2-chloro-N-cyclohexylpyrimidin-4-amine (864655-05-0)

Conditions	Yield
In tetrahydrofuran at 50℃; for 12h;	95%
With diisopropylamine In 1,4-dioxane at 20℃; for 6h;	63%
With sodium hydrogencarbonate In methanol at 20℃; for 6h;	54%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + (R,R)-2,3-butandiol (24347-58-8) → (2R,3R)-3-[(5-bromo-2-chloropyrimidin-4-yl)oxy]butan-2-ol (851008-29-2)

Conditions	Yield
Stage #1: (R,R)-2,3-butandiol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.166667h; Stage #2: 2,4-dichloro-5-bromopyrimidine In tetrahydrofuran at 20℃; for 12h;	81%
Stage #1: (R,R)-2,3-butandiol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.166667h; Stage #2: 2,4-dichloro-5-bromopyrimidine In tetrahydrofuran at 0 - 20℃; for 12h;	81%
Stage #1: (R,R)-2,3-butandiol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 2,4-dichloro-5-bromopyrimidine In tetrahydrofuran at 0 - 20℃; for 12h;	57%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + N-{3-[(3-cyano-propyl)-methanesulfonyl-amino]-phenyl}-acetamide (936920-11-5) → N-(3-{[4-(5-bromo-2-chloro-pyrimidin-4-ylamino)-butyl]-methanesulfonyl-amino}-phenyl)-acetamide

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine; N-{3-[(3-cyano-propyl)-methanesulfonyl-amino]-phenyl}-acetamide With hydrogenchloride; hydrogen; platinum(IV) oxide In ethanol; water at 20℃; under 760.051 Torr; for 5h; Stage #2: 2,4-dichloro-5-bromopyrimidine With triethylamine In acetonitrile at 20℃; for 16h;	43%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 2,2-dimethoxyethylamine (22483-09-6) → 5-bromo-2-chloro-N-(2,2-dimethoxyethyl)pyrimidin-4-amine

Conditions	Yield
With triethylamine In ethanol at 20℃; for 24h;	83%
With triethylamine In ethanol at 0 - 20℃; for 12h;	77%
Stage #1: 2,4-dichloro-5-bromopyrimidine; 2,2-dimethoxyethylamine In ethanol at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With triethylamine In ethanol Inert atmosphere;	64%
With triethylamine In ethanol at 0 - 20℃; for 16.25h;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + D-alanine methyl ester hydrochloride (14316-06-4) → methyl N-(5-bromo-2-chloropyrimidin-4-yl)-D-alaninate (851008-31-6)

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 48h;	86%
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 48h;	86%
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 48h;	86%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + meta-nitrophenol (554-84-7) → 5-bromo-2-chloro-4-(3-nitrophenoxy)pyrimidine

Conditions	Yield
Stage #1: meta-nitrophenol With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 2,4-dichloro-5-bromopyrimidine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃;	93%
With potassium carbonate In N,N-dimethyl-formamide
With N-ethyl-N,N-diisopropylamine In ethanol at 0 - 20℃;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 4-fluoroaniline (371-40-4) → 5-bromo-2-chloro-4-[(4-fluorophenyl)amino]-pyrimidine (280582-07-2)

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 20℃; for 18h;	90%
With potassium carbonate In water; isopropyl alcohol at 20℃; for 18h;	90%
With sodium carbonate In ethanol at 20℃; for 16h;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + sodium methylate (124-41-4) → 5-bromo-2-chloro-4-methoxypyrimidine (57054-92-9)

Conditions	Yield
With methanol at 20℃; for 4h;	93%
In methanol at 20℃; for 4h; Cooling with ice;	93%
In methanol at 20℃; for 12h;	90%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (144222-22-0) → 4-[(5-bromo-2-chloro-pyrimidin-4-ylamino)methyl]-piperidine-1-carboxylic acid tert-butyl ester (1289114-86-8)

Conditions	Yield
With trimethylamine In acetonitrile at 20℃; for 2h;	92%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;	75%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 0.333333h; Microwave irradiation;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 4-methoxy-aniline (104-94-9) → 5-bromo-2-chloro-N-(4-methoxyphenyl)pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 100℃;	72%
With potassium carbonate In water; isopropyl alcohol at 20℃;	51.4%
Stage #1: 2,4-dichloro-5-bromopyrimidine; 4-methoxy-aniline In isopropyl alcohol at 20℃; Stage #2: With potassium carbonate In water at 20℃;	51.4%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 5-aminobenzimidazole (934-22-5) → (1H-Benzoimidazol-5-yl)-(5-bromo-2-chloro-pyrimidin-4-yl)-amine (852357-08-5)

Conditions	Yield
With sodium carbonate In ethanol at 20℃; for 24h;	93%
With sodium carbonate In ethanol at 20℃; for 16h;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 2,2-dimethylpropylamine (5813-64-9) → (5-bromo-2-chloropyrimidin-4-yl)-(2,2-dimethylpropyl)amine

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	70%
With sodium hydrogencarbonate In methanol at 20℃; for 6h;
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h;

2,4-dichloro-5-bromopyrimidine (36082-50-5) + sodium thiomethoxide (5188-07-8) → 5-bromo-2-chloro-4-(methylthio)pyrimidine (59549-51-8)

Conditions	Yield
In acetonitrile at 20℃;	82.8%
In acetonitrile at 20℃; for 24h;	70%
In acetonitrile at 20℃; for 24h;	70%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,4-dichloro-5-pyrimidinecarboxaldehyde (871254-61-4)

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With TurboGrignard In tetrahydrofuran at -78℃; for 2h; Bouveault Aldehyde Synthesis; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - -42℃; for 12h;	38%
Stage #1: 2,4-dichloro-5-bromopyrimidine With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - -35℃; for 4h;	31%
Stage #1: 2,4-dichloro-5-bromopyrimidine With hydrogenchloride In tetrahydrofuran at -78 - 35℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 2h;	28%

4-morpholinecarboxaldehyde (4394-85-8) + 2,4-dichloro-5-bromopyrimidine (36082-50-5) → 2,4-dichloro-5-pyrimidinecarboxaldehyde (871254-61-4)

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With TurboGrignard In tetrahydrofuran at -78 - -42℃; for 1.25h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78 - -42℃; for 3.91667h;	87%
Stage #1: 2,4-dichloro-5-bromopyrimidine With TurboGrignard In tetrahydrofuran at 78℃; for 1h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78 - -35℃; for 1.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at -35℃;	71%

indole (120-72-9) + 2,4-dichloro-5-bromopyrimidine (36082-50-5) → 3-(5-Bromo-2-chloropyrimidin-4-yl)-1H-indole (1356962-87-2)

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With aluminum (III) chloride In 1,2-dichloro-ethane at 80℃; for 0.5h; Stage #2: indole In 1,2-dichloro-ethane at 80℃; for 18h;	98%
Stage #1: indole With methylmagnesium bromide In tetrahydrofuran; diethyl ether at 0℃; for 0.75h; Inert atmosphere; Stage #2: 2,4-dichloro-5-bromopyrimidine In tetrahydrofuran; diethyl ether at 0 - 60℃; for 2.25h; Inert atmosphere;	75%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + m-bromobenzoic aldehyde (3132-99-8) → (3-bromo-phenyl)-(2,4-dichloro-pyrimidin-5-yl)-methanol (1386399-13-8)

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With isopropylmagnesium chloride In tetrahydrofuran at -35℃; for 1h; Inert atmosphere; Stage #2: m-bromobenzoic aldehyde In tetrahydrofuran at -35℃; for 2h; Inert atmosphere; Stage #3: With water In tetrahydrofuran Inert atmosphere;	98.8%
Stage #1: 2,4-dichloro-5-bromopyrimidine With isopropylmagnesium chloride In tetrahydrofuran at -35℃; for 1h; Inert atmosphere; Stage #2: m-bromobenzoic aldehyde at -35℃; for 2h;	98.8%

2,4-dichloro-5-bromopyrimidine (36082-50-5) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(5-bromo-2-chloropyrimidin-4-yl)piperazine-1-carboxylate (1289198-78-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 30℃; for 2h;	89%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 0.333333h; Microwave irradiation;

Upstream product

• 51-20-7 5-bromouracil 
• 51-20-7 2,4-dihydroxy-5-bromopyrimidine 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 113138-12-8 5-bromo-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 

Downstream Products

• 56686-16-9 5-bromo-2,4-dimethoxypyrimidine 
• 132164-47-7 2,4-diethoxy-5-bromopyrimidine 
• 122372-11-6 5-bromo-2-chloro-4-(β-styryl)pyrimidine 
• 41244-53-5 5-bromo-2,4-bis(benzyloxy)pyrimidine 
• 205672-19-1 2-chloro-4-benzyloxy-5-bromopyrimidine 
• 57054-86-1 (5-bromo-2-chloro-pyrimidin-4-yl)-dimethyl-amine 
• 205672-24-8 5-bromo-2-chloro-N-methyl-pyrimidin-4-amine 
• 205672-25-9 4-amino-5-bromo-2-chloropyrimidine 
• 280581-50-2 5-bromo-2-chloro-N-phenylpyrimidin-4-amine 
• 664988-37-8 5-bromo-2,4-bis(4-methoxybenzyloxy)pyrimidine 
• 280582-07-2 5-bromo-2-chloro-4-[(4-fluorophenyl)amino]-pyrimidine 
• 761440-02-2 2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-N-propyl-benzenesulfonamide 
• 19752-61-5 5-bromo-2,4-di(tert-butoxy)pyrimidine 
• 325702-64-5 2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-benzoic acid 

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The invention discloses a preparation method, namely BTC and SOCl, of a chloropolyhydroxyl aza heteroaromatic ring compound as a raw material with a polyhydroxy aza heteroaromatic ring compound as a raw material, and a preparation method thereof. 2 As the double chlorination reagent, a chloropolyhydroxyl aza-aromatic ring compound is produced by chlorination reaction with 4 - dimethylaminopyridine (DMAP) as a catalyst at room temperature to reflux temperature of the reaction, as a catalyst. BTC TC TC TC2 /DMDMAP chlorination system has high efficiency, high selectivity and chlorine substitution on a polyhydroxy nitrogen heterocyclic compound; the system can replace POCl3 , The production of phosphorus-containing wastewater is avoided. Using BTC as a chlorination reagent, the reaction by-product was HCl and CO. 2 . From the aspects of industrial wastewater treatment, environmental protection and the like, the advantages thereof are obvious; SOCl is distilled off after the reaction is ended. 2 The quantity is almost no loss, can be used repeatedly, and reduces the process cost. (by machine translation)

Preparation method for 2,4-dichloropyrimidine and derivatives thereof

The invention discloses a preparation method for 2,4-dichloropyrimidine and derivatives thereof. A catalyst, a compound 1 and phosgene are involved in the preparation method. The compound 1 reacts with the phosgene under the action of the catalyst in a solvent. The preparation method is reasonably designed, is convenient for use and is capable of solving the problems of high discharge of phosphorus wastewater and environmental pollution of the traditional process; the end product prepared according to the method is high in conversion rate, the preparation period is short and the problem of environmental pollution is reduced; the method is energy-saving and environment-friendly and is suitable for extensive promotion.

Preparation method for halogenated uracil compounds

The invention discloses a preparation method for halogenated uracil compounds as shown in a formula 2 which is described in the specification. The preparation method comprises a step of subjecting a compound 1 and PCl5 to a chlorination reaction in a solvent. X in the formula is F, Cl, Br or I. The solvent is one or more selected from a group consisting of SOCl2, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene and 1,1,2-trichloroethane. The preparation method uses 5-halouracil as a starting material, and is simple in process, high in yield, friendly to environment and suitable for industrial production.

Synthesis, characterization, and in vitro evaluation of the selective P2Y2 receptor antagonist AR-C118925

The Gq protein-coupled, ATP- and UTP-activated P2Y2 receptor is a potential drug target for a range of different disorders, including tumor metastasis, inflammation, atherosclerosis, kidney disorders, and osteoporosis, but pharmacological studies are impeded by the limited availability of suitable antagonists. One of the most potent and selective antagonists is the thiouracil derivative AR-C118925. However, this compound was until recently not commercially available and little is known about its properties. We therefore developed an improved procedure for the synthesis of AR-C118925 and two derivatives to allow up-scaling and assessed their potency in calcium mobilization assays on the human and rat P2Y2 receptors recombinantly expressed in 1321N1 astrocytoma cells. The compound was further evaluated for inhibition of P2Y2 receptor-induced β-arrestin translocation. AR-C118925 behaved as a competitive antagonist with pA2 values of 37.2?nM (calcium assay) and 51.3?nM (β-arrestin assay). Selectivity was assessed vs. related receptors including P2X, P2Y, and adenosine receptor subtypes, as well as ectonucleotidases. AR-C118925 showed at least 50-fold selectivity against the other investigated targets, except for the P2X1 and P2X3 receptors which were blocked by AR-C118925 at concentrations of about 1?μM. AR-C118925 is soluble in buffer at pH 7.4 (124?μM) and was found to be metabolically highly stable in human and mouse liver microsomes. In Caco2 cell experiments, the compound displayed moderate permeability indicating that it may show limited peroral bioavailability. AR-C118925 appears to be a useful pharmacological tool for in vitro and in vivo studies.

Symmetric pyrimidyl iodonium salt and preparation method thereof

The invention relates to symmetric pyrimidyl iodonium salt and a preparation method thereof. The structural formula of the symmetric pyrimidyl iodonium salt is shown in the description. The preparation method comprises the steps that alcohol reacts with sodium hydride, then the reaction product drips into the reaction product of 5-bromouracil and phosphorus oxychloride, the reaction product reacts with a butyl lithium reagent after reaction and then reacts with simple substance iodine and organic metal halide respectively to obtain a 5-iodine-2,4-dialkoxyl pyrimidine and a metal pyrimidine derivative; the 5-iodine-2,4-dialkoxyl pyrimidine reacts with a nitrogen-fluorine reagent and TMSX-1 to obtain a 2,4-dialkyl pyrimidyl trivalent iodine intermediate and then reacts with TMSX-2 and the metal pyrimidine derivative, then anionic sodium or potassium salt is added to perform extraction, and the symmetric pyrimidyl iodonium salt is obtained. The oxidation method adopted by the preparation method of the symmetric pyrimidyl iodonium salt is acid-free, efficient and moderate. The symmetric pyrimidyl iodonium salt is used for efficient preparation of PET tracer agent F-5-fluorouracil, and the poor problems of poor selectivity, low productivity, difficult separation and the like are avoided.

Synthesis and coordination chemistry of pyrimidine-substituted phosphine ligands

Reaction of PPh2H with UrI (Ur = uracil) in the presence of Pd(OAc)2 affords PPh2Ur. In the solid state, PPh 2Ur crystallises as a methanol solvate in the monoclinic space group P21/c. Reaction of PPh2Ur with CuI in dry and deoxygenated THF solution results in the formation of [Cu4(μ3-I) 4(PPh2Ur)4]. A single crystal X-ray diffraction study demonstrated that this species contains a distorted tetrahedral core of copper atoms, with facially-capping iodides. The uracil groups in the clusters are engaged in hydrogen bonding to groups on neighbouring molecules to form an extended array. A similar reaction between PPh2Ur and CuI in unpurified THF allows for the isolation of the phosphine oxide P(O)PPh 2Ur. The synthesis of the benzyl-protected phosphine PPh 2UrP is also described [UrP = 2,4-bis(benzyloxy)pyrimidine]. Reaction of PPh2UrP with [Ru(η5-C5H5)(NCMe)3]PF 6 allows for isolation of [Ru(η5-C5H 5)(NCMe)(PPh2UrP)2]PF6.

Synthesis and structure-activity relationships of a novel series of pyrimidines as potent inhibitors of TBK1/IKKε kinases

The design, synthesis and structure-activity relationships of a novel series of 2,4-diamino-5-cyclopropyl pyrimidines is described. Starting from BX795, originally reported to be a potent inhibitor of PDK1, we have developed compounds with improved selectivity and drug-like properties. These compounds have been evaluated in a range of cellular and in vivo assays, enabling us to probe the putative role of the TBK1/IKKε pathway in inflammatory diseases.

Large-scale solvent-free chlorination of hydroxy-pyrimidines,-pyridines,- pyrazines and-amides using equimolar POCl3

Chlorination with equimolar POCl3 can be efficiently achieved not only for hydroxypyrimidines, but also for many other substrates such as 2-hydroxy-pyridines,-quinoxalines, or even-amides. The procedure is solvent-free and involves heating in a sealed reactor at high temperatures using one equivalent of pyridine as base. It is suitable for large scale (multigram) batch preparations.