37131-89-8

Basic information

• Product Name: 2,4-Dichloropyrimidine-5-carboxylic acid
• Synonyms: 2,4-Dichloro-5-pyrimidinecarboxylic acid;2,4-Dichloropyrimidine-5-carboxylic acid;5-PyriMidinecarboxylic acid, 2,4-dichloro-
• CAS NO: 37131-89-8
• Molecular Formula: C₅H₂Cl₂N₂O₂
• Molecular Weight: 192.99
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 37131-89-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 96-97 °C
• Boiling Point: 368.384 °C at 760 mmHg
• Flash Point: 176.592 °C
• Appearance: /
• Density: 1.718
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 0.97±0.32(Predicted)
• CAS DataBase Reference: 2,4-Dichloropyrimidine-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloropyrimidine-5-carboxylic acid(37131-89-8)
• EPA Substance Registry System: 2,4-Dichloropyrimidine-5-carboxylic acid(37131-89-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 37131-89-8(Hazardous Substances Data)

Usage

General Description

2,4-Dichloropyrimidine-5-carboxylic acid is a chemical compound with the molecular formula C6H3Cl2N2O2. It is a white crystalline solid that is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also utilized in the production of fungicides and herbicides. 2,4-Dichloropyrimidine-5-carboxylic acid is known for its ability to inhibit the growth of certain bacteria and fungi, making it an important ingredient in the development of antimicrobial agents. Additionally, 2,4-Dichloropyrimidine-5-carboxylic acid is used as a building block in the manufacturing of various organic compounds, and its derivatives have been studied for potential applications in the fields of medicine and materials science.

InChI:InChI=1/C5H2Cl2N2O2/c6-3-2(4(10)11)1-8-5(7)9-3/h1H,(H,10,11)

Synthetic route

2,4-dihydroxypyrimidine-5-carboxylic acid (23945-44-0) → 2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate Reflux;	100%
With N,N-diethylaniline; trichlorophosphate In N,N-dimethyl-formamide at 90℃; for 2.66667h; Under cold conditions;	65%
With N,N-diethylaniline; trichlorophosphate
With N,N-dimethyl-aniline; trichlorophosphate at 110℃; for 4h; Cooling with ice;

2,4-dichloropyrimidine-5-carbonyl chloride (2972-52-3) → 2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8)

Conditions	Yield
With water In diethyl ether at 35℃; for 1h;	93%
With water In tetrahydrofuran at 20℃; for 0.83h;

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + 6-nitropyridine-2-sulfonamide (75903-60-5) → 2,4-dichloro-N-((6-nitropyridin-2-yl)sulfonyl)pyrimidine-5-carboxamide

Conditions	Yield
Stage #1: 2,4-dichloropyrimidine-5-carboxylic acid With thionyl chloride for 2h; Reflux; Stage #2: 6-nitropyridine-2-sulfonamide With triethylamine In dichloromethane at 20℃; for 0.5h;	100%
Stage #1: 2,4-dichloropyrimidine-5-carboxylic acid With thionyl chloride for 1h; Reflux; Stage #2: 6-nitropyridine-2-sulfonamide With trimethylamine In dichloromethane at 20℃; for 0.5h;	100%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → 2,4-dichloropyrimidine-5-carbonyl chloride (2972-52-3)

Conditions	Yield
With thionyl chloride at 80℃; for 4h;	90%
With phosphorus pentachloride; trichlorophosphate at 115℃; for 6h;	64%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
With thionyl chloride Reflux;

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + 2,6-dimethyl-4-fluoroaniline (392-70-1) → C13H10Cl2FN3O (1099657-26-7)

Conditions	Yield
With Amberlyst A-21 resin In ethyl acetate at 50℃;	90%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + aniline (62-53-3) → 2,4-dichloro-N-phenylpyrimidin-5-carboxamide (1099657-22-3)

Conditions	Yield
With Amberlyst A-21 resin In ethyl acetate at 50℃;	90%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + 2,6-dimethylaniline (87-62-7) → 2,4-dichloro-N-(2,6-dimethylphenyl)pyrimidin-5-carboxamide (835633-82-4)

Conditions	Yield
With Amberlyst A-21 resin In ethyl acetate at 50℃;	90%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + 2,4,6-trimethylaniline (88-05-1) → C14H13Cl2N3O (1099657-28-9)

Conditions	Yield
With Amberlyst A-21 resin In ethyl acetate at 50℃;	90%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + 2,6-Dichloroaniline (608-31-1) → 2,4-dichloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide (835633-83-5)

Conditions	Yield
With Amberlyst A-21 resin In ethyl acetate at 50℃;	90%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + N-Boc-1,3-diaminopropane (75178-96-0) → 4-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acid (1314997-89-1)

Conditions	Yield
With triethylamine In tetrahydrofuran; ethyl acetate at 2 - 20℃; for 0.5h;	88.6%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,4-dichloro-7-hydroxyfuro[3,4-d]pyrimidin-5(7H)-one

Conditions	Yield
Stage #1: 2,4-dichloropyrimidine-5-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran for 0.333333h; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran for 1h;	70%

4-aminotricyclo[3.3. 1.13,7]decan-1-ol + 2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → C15H17Cl2N3O2

Conditions	Yield
Stage #1: 2,4-dichloropyrimidine-5-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: 4-aminotricyclo[3.3. 1.13,7]decan-1-ol With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide at 0℃; for 4h;	66%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + 1-Amino-2-methyl-propan-2-ol (2854-16-2) → 2-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid (1315513-37-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 2 - 20℃;	59%

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + Cyclopentamine (1003-03-8) → 2-chloro-4-(cyclopentylamino)pyrimidine-5-carboxylic acid (1314997-73-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 2 - 20℃; for 2h;	42%

spiro[2.5]octan-6-ylmethanol (849671-56-3) + 2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → 2-chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 1.5h;

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + ethylamine (75-04-7) → 2-chloro-4-(ethylamino)pyrimidine-5-carboxylic acid (101683-59-4)

Conditions	Yield
With triethylamine In tetrahydrofuran; water at 20℃; for 1.75h;

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → tert-Butyl [3-(2-chloro-5-fluorocarbonylpyrimidin-4-ylamino)propyl]-carbamate (1314997-90-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / ethyl acetate; tetrahydrofuran / 0.5 h / 2 - 20 °C 2: triethylamine; trifluoro-[1,3,5]triazine / dichloromethane / 2 h / 20 °C View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → 2-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid fluoride (1315513-38-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 2 - 20 °C 2: triethylamine; trifluoro-[1,3,5]triazine / dichloromethane / 20 °C View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → 2-chloro-4-(ethylamino)pyrimidine-5-carboxylic acid fluoride

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / water; tetrahydrofuran / 1.75 h / 20 °C 2: triethylamine; trifluoro-[1,3,5]triazine / dichloromethane / 3 h View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → 2-chloro-4-(cyclopentylamino)pyrimidine-6-carboxylic acid fluoride (1314997-74-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 2 h / 2 - 20 °C 2: triethylamine; trifluoro-[1,3,5]triazine / dichloromethane / 4 h / 20 °C View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → C19H28N4O2S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C 1.2: 4 h / 0 °C 2.1: sodium carbonate / N,N-dimethyl acetamide / 4 h / 25 °C 3.1: tetrahydrofuran / 6 h / 150 °C / Microwave irradiation View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → C22H32N4O4

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C 1.2: 4 h / 0 °C 2.1: sodium hexamethyldisilazane / 2 h / 150 °C / Microwave irradiation 3.1: 10 h / 150 °C / Microwave irradiation View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → C18H24ClN3O2S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C 1.2: 4 h / 0 °C 2.1: sodium carbonate / N,N-dimethyl acetamide / 4 h / 25 °C View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → C18H24ClN3O3

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C 1.2: 4 h / 0 °C 2.1: sodium hexamethyldisilazane / 2 h / 150 °C / Microwave irradiation View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → 2-dimethylamino-N-[(2r,5s)-5-hydroxyadamantan-2-yl]-4-propylsulfanylpyrimidine-5-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C 1.2: 4 h / 0 °C 2.1: sodium carbonate / N,N-dimethyl acetamide / 4 h / 25 °C 3.1: tetrahydrofuran / 6 h / 150 °C / Microwave irradiation View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → N-((6-aminopyridin-2-yl)sulfonyl)-2,4-dichloropyrimidine-5-carboxamide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride / 2 h / Reflux 1.2: 0.5 h / 20 °C 2.1: hydrogenchloride; water; iron / tetrahydrofuran; ethanol / 1 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / 1 h / Reflux 1.2: 0.5 h / 20 °C 2.1: hydrogenchloride / water; ethanol; tetrahydrofuran / 1 h / 60 °C View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → (S )-N-((6-aminopyridin-2-yl)sulfonyl)-2-chloro-4-(2,2,4-trimethylpyrrolidin-1-yl)pyrimidine-5-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 2 h / Reflux 1.2: 0.5 h / 20 °C 2.1: hydrogenchloride; water; iron / tetrahydrofuran; ethanol / 1 h / 60 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 125 °C View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1 h / Reflux 1.2: 0.5 h / 20 °C 2.1: hydrogenchloride / water; ethanol; tetrahydrofuran / 1 h / 60 °C 3.1: potassium carbonate / dimethyl sulfoxide / 20 h / 125 °C / Sealed tube View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) → N-[(6-amino-2-pyridyl)sulfonyl]-2-(3-fluoro-5-isobutoxy-phenyl)-4-[(4S)-2,2,4-trimethylpyrrolidin-1-yl]pyrimidine-5-carboxamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / 2 h / Reflux 1.2: 0.5 h / 20 °C 2.1: hydrogenchloride; water; iron / tetrahydrofuran; ethanol / 1 h / 60 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 125 °C 4.1: sodium carbonate / 1,4-dioxane / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1 h / Reflux 1.2: 0.5 h / 20 °C 2.1: hydrogenchloride / water; ethanol; tetrahydrofuran / 1 h / 60 °C 3.1: potassium carbonate / dimethyl sulfoxide / 20 h / 125 °C / Sealed tube 4.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 120 °C / Microwave irradiation; Inert atmosphere View Scheme

2,4-dichloro-5-pyrimidinecarboxylic acid (37131-89-8) + Cyclopropylamine (765-30-0) → 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylic acid (1192711-37-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 0.166667h; Microwave irradiation;

Upstream product

• 23945-44-0 2,4-dihydroxypyrimidine-5-carboxylic acid 
• 2972-52-3 2,4-dichloropyrimidine-5-carbonyl chloride 

Downstream Products

• 835633-83-5 2,4-dichloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide 
• 1099657-28-9 C₁₄H₁₃Cl₂N₃O 
• 835633-82-4 2,4-dichloro-N-(2,6-dimethylphenyl)pyrimidin-5-carboxamide 
• 1099657-22-3 2,4-dichloro-N-phenylpyrimidin-5-carboxamide 
• 1099657-26-7 C₁₃H₁₀Cl₂FN₃O 
• 2972-52-3 2,4-dichloropyrimidine-5-carbonyl chloride 

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