2927-71-1

Basic information

• Product Name: 2,4-Dichloro-5-fluoropyrimidine
• Synonyms: CHEMPACIFIC 37950;5-FLUORO-2,4-DICHLOROPYRIMIDINE;2,4-DICHLORO-5-FLUOROPYRIMIDINE;2,4-Dichloro-5-fluorouracil;5-Fluoro-2,4-dichloropyrimdine;2,6-DICHLORO-5-FLUORORACIL;2,4-Dichloro-5-Fluoropyrimidin;2,4-Dichloro-5-fluoropyrimidine99%
• CAS NO: 2927-71-1
• Molecular Formula: C₄HCl₂FN₂
• Molecular Weight: 166.97
• EINECS: 249-616-3
• Product Categories: Pyrimidine Series;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Halides;Pyrazines, Pyrimidines & Pyridazines;Pyrimidine;Building Blocks;Fluorinated;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Aromatics;Fluorine series
• Mol File: 2927-71-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: 37-41 °C(lit.)
• Boiling Point: 80 °C / 16mmHg
• Flash Point: 223 °F
• Appearance: White to pale brown/Powder or Crystalline Powder or Low Melting Solid
• Density: 1.605 g/cm³
• Vapor Pressure: 0.148mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• PKA: -3.96±0.29(Predicted)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 2,4-Dichloro-5-fluoropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-5-fluoropyrimidine(2927-71-1)
• EPA Substance Registry System: 2,4-Dichloro-5-fluoropyrimidine(2927-71-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34-22
• Safety Statements: 26-36-37/39-45-36/37/39
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 2927-71-1(Hazardous Substances Data)

Usage

Chemical Properties

2,4-Dichloro-5-fluoropyrimidine is Yellow to Orange Crystalline Solid

Uses

Different sources of media describe the Uses of 2927-71-1 differently. You can refer to the following data:
1. 2,4-Dichloro-5-fluoropyrimidine is used in the synthesis of two glucuronic derivatives of 5-fluorouracil as neoplasm inhibitors. It is used in the synthesis of two glucuronic derivatives of 5-fluorouracil as neoplasm inhibitors.
2. 2,4-Dichloro-5-fluoropyrimidine can be used as a starting material to synthesize: 5-fluoropyrimidine-2-carboxamides and 5-fluoropyrimidine-4-carboxamides as potential kinase inhibitors. A series of 2,4-diamino-5-fluoropyrimidine derivatives as potential protein kinase Cθ inhibitors. 2,4-Bisanilinopyrimidine derivatives as potential aurora kinases inhibitors. 5-fluoro-N,N-bis(4-methoxyphenyl)-2,4-pyrimidinediamine by reacting with p-methoxy aniline in the presence of DIPEA. 2-chloro-5-fluoro-4-(4-fluorophenyl)pyrimidine by Suzuki coupling reaction in the presence of (4-fluorophenyl)boronic acid triphenylphosphine, and palladium(II) acetate catalyst. 5-fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine, a scaffold, which is used in the preparation of potent deoxycytidine kinase inhibitors.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C4HCl2FN2/c5-3-2(7)1-8-4(6)9-3/h1H

Synthetic route

2,4-dimethoxy-5-fluoropyrimidine (4330-22-7) → 2,4-dichloro-5-fluoropyrimidine (2927-71-1)

Conditions	Yield
Stage #1: 5-fluoro-2,4-dimethoxypyrimidine With thionyl chloride In chloroform at 0℃; for 0.5h; UV-irradiation; Stage #2: With chlorine In chloroform at 20℃; for 12h; Solvent; Wavelength; UV-irradiation;	98%

5-fluoropyrimidine-2,4-diol (51-21-8) → 2,4-dichloro-5-fluoropyrimidine (2927-71-1)

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-aniline at 100℃; for 13h; Inert atmosphere; Large scale;	95%
With pyridine; trichlorophosphate at 180℃; under 150.015 - 900.09 Torr; for 2h; Neat (no solvent);	93%
With dimethyl amine; trichlorophosphate at 95 - 120℃; for 4h;	92%

5-fluorouracil (51-21-8) → 2,4-dichloro-5-fluoropyrimidine (2927-71-1)

Conditions	Yield
With dimethyl amine; trichlorophosphate at 95 - 120℃; for 4h;	94%
With phosphorus pentachloride for 4h; Heating;	91%
Stage #1: 5-fluorouracil With trichlorophosphate at 95℃; for 3.5h; Stage #2: With hydrogenchloride In water at 0 - 20℃;	87%

2,4,6-trichloro-5-fluoropyrimidine (6693-08-9) → 2,4-dichloro-5-fluoropyrimidine (2927-71-1)

Conditions	Yield
With hydrogen; triethylamine; palladium on activated charcoal In ethyl acetate at 30℃; under 2625.2 Torr;	87%

ethyl bromide (74-96-4) → 2,4-dichloro-5-fluoropyrimidine (2927-71-1)

Conditions	Yield
With magnesium In tetrahydrofuran

morpholine (110-91-8) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 4-(2-chloro-5-fluoro-pyrimidin-4-yl)morpholine (31646-53-4)

Conditions	Yield
In water at 60 - 70℃; for 2.5h;	100%
With N-ethyl-N,N-diisopropylamine In ethanol Reflux; regioselective reaction;	95%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Reflux;	85%

piperidine (110-89-4) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2-chloro-5-fluoro-4-piperidin-1-yl-pyrimidine (40423-82-3)

Conditions	Yield
In water at 60 - 70℃; for 2.5h;	100%

1-n-propylpiperazine (21867-64-1) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2-Chloro-5-fluoro-4-(4-propyl-piperazin-1-yl)-pyrimidine

Conditions	Yield
In water at 60 - 70℃; for 2.5h;	100%

2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2-chloro-5-fluoropyrimidin-4-amine (155-10-2)

Conditions	Yield
With ammonium hydroxide at 60 - 70℃; for 2.5h;	100%
With ammonia In water Substitution;
With ammonium hydroxide In ethanol at 25 - 35℃; for 3.5h;

(R)-tert-butyl (1-aminobutan-2-yl)carbamate (956125-05-6) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → {(R)-1-[(2-Chloro-5-fluoro-pyrimidin-4-ylamino)-methyl]-propyl}-carbamic acid tert-butyl ester (956125-24-9)

Conditions	Yield
With triethylamine In acetonitrile at 0℃; for 3h;	100%

4-methoxy-aniline (104-94-9) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 5-fluoro-N2,N4-bis(4-methoxyphenyl)pyrimidine-2,4-diamine diformate

Conditions	Yield
Stage #1: 4-methoxy-aniline; 2,4-dichloro-5-fluoropyrimidine With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 160℃; for 0.333333h; Microwave irradiation; Stage #2: With formic acid In water; acetonitrile	100%

4-fluoroboronic acid (1765-93-1) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2-chloro-5-fluoro-4-(4-fluorophenyl)pyrimidine (1341200-71-2)

Conditions	Yield
With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water for 12h; Suzuki coupling; Reflux;	100%

(S)-1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (1537256-09-9) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → (S)-2-chloro-5-fluoro-N-(1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidin-4-amine (1537207-28-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 1h; Microwave irradiation;	100%

n-propylmagnesium bromide (927-77-5) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2,4-dichloro-5-fluoro-6-propylpyrimidine

Conditions	Yield
Stage #1: n-propylmagnesium bromide; 2,4-dichloro-5-fluoropyrimidine In tetrahydrofuran; 1,2-dimethoxyethane at 15℃; for 1h; Stage #2: With iodine; triethylamine In tetrahydrofuran; 1,2-dimethoxyethane at 5℃;	100%

cyclopropanol (16545-68-9) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2-chloro-4-cyclopropoxy-5-fluoropyrimidine

Conditions	Yield
Stage #1: cyclopropanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Stage #2: 2,4-dichloro-5-fluoropyrimidine In tetrahydrofuran; mineral oil at 0℃; for 4h;	100%

2,4-dichloro-5-fluoropyrimidine (2927-71-1) + 4-fluoroaniline (371-40-4) → 2-chloro-5-fluoro-N-(4-fluorophenyl)pyrimidin-4-amine (1049666-34-3)

Conditions	Yield
With trifluoroacetic acid In ethanol at 20℃; for 24h; regioselective reaction;	99%
In methanol; water at 50℃; for 5h;	68%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 80℃; for 1.5h;

Nα-isobutyl-Nβ-Boc-hydrazine (57699-53-3) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → C13H20ClFN4O2 (929016-08-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol Reflux;	99%

7-fluoro-2,3,3-trimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-indole + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 5-(2-chloro-5-fluoropyrimidin-4-yl)-7-fluoro-2,3,3-trimethyl-3H-indole

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 130℃; for 1h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	99%
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 130℃; for 1h; Microwave irradiation; Inert atmosphere;	301.2 mg

2-pyridylmethyl 4-tolyl sulfone (58414-96-3) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2-Chloro-10-(toluene-4-sulfonyl)-pyrimido[4,5-b]indolizine (137890-00-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Heating;	98%

2,4-dichloro-5-fluoropyrimidine (2927-71-1) + Diethyl methylmalonate (609-08-5) → 2-methyl-2-(2-chloro-5-fluoropyrimidinyl-4-yl)-1,3-propanedioic acid diethyl ester (137234-89-0)

Conditions	Yield
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran; mineral oil at -10℃; for 0.5h; Stage #2: 2,4-dichloro-5-fluoropyrimidine In tetrahydrofuran; mineral oil at -10℃; for 0.5h;	98%
With sodium hydride In tetrahydrofuran; mineral oil at -10℃; for 0.5h;	83%

1-(4-{4-amino-3-methoxyphenyl}piperazine-1-yl)ethan-1-one (1021426-42-5) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 1-(4-(4-((2-chloro-5-fluoropyrimidin-4-yl)amino)-3-methoxyphenyl)piperazin-1-yl)ethanone (1474014-16-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Temperature;	98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	68%

2,4-dichloro-5-fluoropyrimidine (2927-71-1) + 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (847818-74-0) → 2-chloro-5-fluoro-4-(1-methyl-1H-pyrazol-5-yl)pyrimidine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In tetrahydrofuran; water Reflux;	98%

N-(1,3-benzodioxol-5-ylmethyl)-2-(tetrahydro-2H-pyran-4-yl)ethanamine + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → N-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5-fluoro-N-[2-(tetrahydro-2H-pyran-4-yl)ethyl]pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 85℃;	98%

methyl 6-azaspiro[2.5]octane-1-carboxylate hydrochloride + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → methyl 6-(2-chloro-5-fluoropyrimidin-4-yl)-6-azaspiro[2.5]octane-1-carboxylate

Conditions	Yield
With triethylamine In methanol at 30℃; for 16h;	98%

3-methyl-5-aminopyrazole (31230-17-8) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → 2-chloro-5-fluoro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (851434-99-6)

Conditions	Yield
With triethylamine In ethanol at 0 - 25℃; regioselective reaction;	97%
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 48h; Inert atmosphere;	86%
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 48h; Inert atmosphere;	86%
With triethylamine In ethanol at 18 - 25℃; for 12h;
With triethylamine In ethanol at 18 - 25℃; for 12h;

2-fluorobenzylamine (89-99-6) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → (2-chloro-5-fluoropyrimidin-4-yl)-(2-fluorobenzyl)amine (1174385-80-8)

Conditions	Yield
With triethylamine In tetrahydrofuran for 5h; Reflux;	97%
With triethylamine In tetrahydrofuran at 80℃; for 5h;	97%

N-(1,3-benzodioxol-5-ylmethyl)-3-(5-phenyl-1,2,4-oxadiazol-3-yl)propan-1-amine + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → N-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5-fluoro-N-[3-(5-phenyl-1,2,4-oxadiazol-3-yl)propyl]pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 85℃;	97%

tert-butyl 3-hydroxyphenylcarbamate (19962-06-2) + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → C15H15ClFN3O3 (1246610-46-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 110℃; for 16h;	96%

2,4-dichloro-5-fluoropyrimidine (2927-71-1) + sodium thiomethoxide (5188-07-8) → 2-chloro-5-fluoro-4-methylthiopyrimidine

Conditions	Yield
In tetrahydrofuran at -30℃; for 2h;	96%
In tetrahydrofuran; water at -30℃; for 2h;	93%
In tetrahydrofuran at 20℃; for 12h;

N-(1,3-benzodioxol-5-ylmethyl)-1-methylcyclopropanamine + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → N-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5-fluoro-N-(1-methylcyclopropyl)pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 85℃;	96%

N-(1,3-benzodioxol-5-ylmethyl)-2-(4-fluorophenyl)ethanamine + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → N-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5-fluoro-N-[2-(4-fluorophenyl)ethyl]pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 85℃;	96%

1-(1,3-benzodioxol-5-yl)-N-(cyclopropylmethyl)methanamine + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → N-(1,3-benzodioxol-5-ylmethyl)-2-chloro-N-(cyclopropylmethyl)-5-fluoropyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol; isopropyl alcohol at 85℃;	96%

N-(1,3-benzodioxol-5-ylmethyl)-2-(4-chloro-3,5-dimethylphenoxy)ethanamine + 2,4-dichloro-5-fluoropyrimidine (2927-71-1) → N-(1,3-benzodioxol-5-ylmethyl)-2-chloro-N-[2-(4-chloro-3,5-dimethylphenoxy)ethyl]-5-fluoropyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 85℃;	96%

Upstream product

• 51-21-8 5-fluorouracil 
• 51-21-8 5-fluoropyrimidine-2,4-diol 
• 6693-08-9 2,4,6-trichloro-5-fluoropyrimidine 
• 74-96-4 ethyl bromide 
• 4330-22-7 5-fluoro-2,4-dimethoxypyrimidine 

Downstream Products

• 137234-87-8 6-Ethyl-5-fluoropyrimidin-4(3H)-one 
• 727422-01-7 2-chloro-5-fluoro-N-(2-methoxyphenyl)pyrimidin-4-amine 
• 1204821-80-6 2-chloro-N⁴-(cyclopropylbenzamide)-5-fluoropyrimidin-4-amine 
• 1158838-41-5 4-((2-chloro-5-fluoropyrimidin-4-yl)amino)-N-(2-chlorophenyl)benzamide 
• 1158838-39-1 2-chloro-N-(4-(2-chloro-5-fluoropyrimidin-4-ylamino)phenyl)-benzamide 
• 1089653-96-2 2-[(2-chloro-5-fluoro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide 
• 1445705-86-1 tert-butyl (R)-2-(((2-chloro-5-fluoropyrimidin-4-yl)amino)methyl)pyrrolidine-1-carboxylate 
• 1474014-16-8 1-(4-(4-((2-chloro-5-fluoropyrimidin-4-yl)amino)-3-methoxyphenyl)piperazin-1-yl)ethanone 

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