37131-89-8

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dichloropyrimidine-5-carboxylic acid is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its chemical properties to contribute to the development of new medications.
Used in Agrochemical Industry:
In the agrochemical sector, 2,4-Dichloropyrimidine-5-carboxylic acid is utilized as a component in the production of fungicides and herbicides, capitalizing on its ability to inhibit microbial growth and thus protect crops from diseases and unwanted vegetation.
Used in Antimicrobial Agents:
2,4-Dichloropyrimidine-5-carboxylic acid is employed as an active ingredient in antimicrobial formulations, due to its efficacy in curbing the proliferation of bacteria and fungi, which is vital for various sanitizing and preservation applications.
Used in Organic Compounds Synthesis:
As a building block, 2,4-Dichloropyrimidine-5-carboxylic acid is used in the manufacturing of a range of organic compounds, highlighting its versatility and importance in organic chemistry and related fields.
Used in Materials Science:
The derivatives of 2,4-Dichloropyrimidine-5-carboxylic acid are studied for their potential applications in materials science, indicating the compound's broad impact and relevance in developing new materials with specific properties.

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 

Relevant academic research and scientific papers

Atorvastatin that non-preparation method

The invention relates to a preparation method of avanafil and a new compound provided in a preparation process. According to the method, 5-uracil carboxylic acid or an ester thereof is taken as the raw material, and the avanafil meeting the clinical requirements can be synthesized at a relatively cost; besides, the preparation method is simple and convenient to operate, mild in reaction conditions, high in yield, low in cost, environmentally friendly and suitable for industrial large-scale production of the avanafil.

5 OXO-5,8-DIHYDROPYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AS CAMKII KINASE INHIBITORS FOR TREATING CARDIOVASCULAR DISEASES

The present invention relates to 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine derivatives, to their preparation and to their therapeutic use.

Identification and optimization of N3,N6-diaryl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamines as a novel class of ACK1 inhibitors

A new series of pyrazolo[3,4-d]pyrimidine-3,6-diamines was designed and synthesized as potent and selective inhibitors of the nonreceptor tyrosine kinase, ACK1. These compounds arose from efforts to rigidify an earlier series of N-aryl pyrimidine-5-carboxamides. The synthesis and structure-activity relationships of this new series of inhibitors are reported. The most promising compounds were also profiled for their pharmacokinetic properties.

COMPOUNDS AND COMPOSITIONS USEFUL AS CATHEPSIN S INHIBITORS

The present invention relates to the use of a 2-cyanopyrimidine compound of the formula (I), wherein R1, R2, R3 and X are as defined in the specification and in the claims, in free form or in salt form, and , where possible, in tautomeric form, as an inhibitor of the activity of cathepsin S.