1193-21-1

Basic information

• Product Name: 4,6-Dichloropyrimidine
• Synonyms: IFLAB-BB F2124-0077;4,6-DICHLOROPYRIMIDINE;PYRIMIDINE, 4,6-DICHLORO-;4 6-DICHLOROPYRIMIDINE 99%;4,6-Dichoropyrimidine;Pyrimidine, 4,6-dichloro- (7CI,8CI,9CI);4,6-DIHYDROXY PYRIMIDINE 99+%;4,6-Dichloropyrimidine ,98%
• CAS NO: 1193-21-1
• Molecular Formula: C₄H₂Cl₂N₂
• Molecular Weight: 148.98
• EINECS: 214-770-2
• Product Categories: PYRIMIDINE;FINE Chemical & INTERMEDIATES;Halides;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;Pyrazines, Pyrimidines & Pyridazines;Nucleotides and Nucleosides;Pyrimidines;Bases & Related Reagents;Nucleotides;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrimidinesHeterocyclic Building Blocks;Heterocycle-Pyrimidine series;alkyl chloride
• Mol File: 1193-21-1.mol

Chemical Properties

• Melting Point: 65-67 °C(lit.)
• Boiling Point: 176 °C(lit.)
• Flash Point: 176°C
• Appearance: Yellow-green/Crystals
• Density: 1.6445 (rough estimate)
• Vapor Pressure: 30-390Pa at 20-50℃
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: -20°C
• Solubility: 95% ethanol: soluble50mg/mL, clear to very slightly hazy, colorl
• PKA: -4.20±0.17(Predicted)
• BRN: 111195
• CAS DataBase Reference: 4,6-Dichloropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dichloropyrimidine(1193-21-1)
• EPA Substance Registry System: 4,6-Dichloropyrimidine(1193-21-1)

Safety Data

• Hazard Codes: C
• Statements: 34-20/21/22-36/37
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3263 8/PG 2
• WGK Germany: 3
• F: 19
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1193-21-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4,6-Dichloropyrimidine is used as a key compound in organic synthesis, serving as a versatile building block for the creation of more complex molecules. Its chemical properties make it a valuable asset in the synthesis of a wide range of compounds.
Used in Synthesis of N-substituted Azacalix[4]pyrimidines:
In the field of macrocyclic chemistry, 4,6-dichloropyrimidine is utilized as a starting reagent for the synthesis of N-substituted azacalix[4]pyrimidines. These macrocyclic compounds have potential applications in various areas, including supramolecular chemistry and molecular recognition.
Used in Synthesis of Disubstituted Pyrimidines:
4,6-Dichloropyrimidine is also employed in the synthesis of disubstituted pyrimidines through a tandem amination and Suzuki-Miyaura cross-coupling process. Disubstituted pyrimidines are important intermediates in the development of pharmaceuticals and agrochemicals, as they can be further modified to create a variety of biologically active molecules.
Used in Biarylpyrimidine Synthesis:
In the synthesis of biarylpyrimidines, which are compounds with potential applications in medicinal chemistry, 4,6-dichloropyrimidine is used as a starting material. The biaryl cross-coupling process allows for the formation of biarylpyrimidine derivatives, which can be further functionalized and studied for their potential therapeutic properties.

Synthesis

The synthesis of 4,6-Dichloropyrimidine is as follows:Dissolve 105.5g of 4,6-diaminopyrimidine in 660.0g of 31% hydrochloric acid and pour into a 2000ml bottle to cool to -5 ° C and dropwise add 500.3g of 33% sodium nitrite. After 2 hours of reaction, HPLC detects 4,6-diamino Pyrimidine is less than 0.5%. 42.8 g of cuprous chloride and 214.0 g of 31% hydrochloric acid are prepared in a 2000 ml bottle. The diazonium salt mother liquor is added dropwise to the bottle. After the dropwise reaction, the reaction is performed at 45 ° C for 2 hours. .Extract with 400g of recovered trichloroethane (200x2 times less than new ones), combine the organic layers for distillation, control the water flush pump 5KPa, temperature 40-140 , collect 404.2g of solvent in the early 40-90 , 90-140 in the later The product was collected at a temperature of 14 ° C to obtain 146.9 g of 4,6-dichloropyrimidine. The yield was 86.4% (based on formazan hydrochloride) and the purity was 99.4%.

InChI:InChI:1S/C4H2Cl2N2/c5-3-1-4(6)8-2-7-3/h1-2H

Synthetic route

5-ethyl-2-methyl-pyridine (104-90-5) + 4,6-pyrimidinediol (1193-24-4) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
With trichlorophosphate	100%
With trichlorophosphate	98%

4,6-pyrimidinediol (1193-24-4) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
With triethylamine; trichlorophosphate at 40 - 105℃; for 2h;	99.1%
With chlorine; magnesium chloride; phosphorus trichloride In trichlorophosphate at 66℃; under 750.075 Torr; for 3.5h; Reagent/catalyst; Temperature; Pressure; Solvent;	99.83%
With bis(trichloromethyl) carbonate; sulfuric acid In N,N-dimethyl-formamide; 1,2-dichloro-benzene at 80℃; for 4.2h; Temperature; Solvent; Industrial scale;	97%

4,6-diaminopyrimidine (2434-56-2) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
Stage #1: 4,6-diaminopyrimidine With hydrogenchloride; sodium nitrite In water at -5℃; for 2h; Stage #2: With hydrogenchloride; copper(l) chloride In water at 45℃; for 2h;	86.4%

phosgene (75-44-5) + 4,6-pyrimidinediol (1193-24-4) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
With 2,3-Dimethylaniline In dichloromethane; water	80%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile

4-chloro-6-methylsulfanylpyrimidine (89283-48-7) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
With sulfuryl dichloride In dichloromethane; acetonitrile at 0℃; for 0.5h;	76%

phosgene (75-44-5) + formamide (77287-34-4, 77287-35-5, 60100-09-6) + acetonitrile (75-05-8) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
at 20 - 140℃; under 982.607 - 20686.5 Torr; for 3h; the Parr Reactor (17328-33);	62.21%
at 105℃; under 5999.08 - 8378.02 Torr; for 3h;
With hydrogenchloride In chlorobenzene at 105℃; under 11739.6 Torr; for 23.5h;

1H-pyrimidine-4,6-dione (25286-58-2) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
With pyridine; trichlorophosphate
With N,N-dimethyl-aniline; trichlorophosphate

C6(2)H6*C4H2Cl2N2 → 4,6-dichloropyrimidine (1193-21-1) + benzene-d6 (1076-43-3)

Conditions	Yield
In tetrachloromethane at 34.9℃; Equilibrium constant;

acetamide (60-35-5) + phosgene (75-44-5) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
In chlorobenzene at 75 - 105℃; under 4913.04 - 17583.5 Torr; for 1.66667 - 23.1667h;

phosgene (75-44-5) + ethyl cyanoformate (623-49-4) + acetonitrile (75-05-8) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
With hydrogenchloride at 52 - 74℃;

phosgene (75-44-5) + aminoketone hydrochloride (25600-32-2) + acetamide hydrochloride (13507-15-8) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
In chlorobenzene at 105℃; under 14997.7 Torr; for 90h;

4-chloro-6-methoxy-pyrimidine (26452-81-3) → 4,6-dichloropyrimidine (1193-21-1)

phosgene (75-44-5) + 4,6-pyrimidinediol (1193-24-4) + Triphenylphosphine oxide (791-28-6) + dichlorotriphenylphosphorane (2526-64-9) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
In chlorobenzene

phosgene (75-44-5) + dmap (1122-58-3) + 4,6-pyrimidinediol (1193-24-4) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
In water; acetonitrile

1H-imidazole (288-32-4) + phosgene (75-44-5) + 4,6-pyrimidinediol (1193-24-4) → 4,6-dichloropyrimidine (1193-21-1)

Conditions	Yield
In acetonitrile

4,6-dichloropyrimidine (1193-21-1) + allylhydrazine (7422-78-8) → 4,6-bis[1-(prop-2-enyl)hydrazino]pyrimidine

Conditions	Yield
for 3h; Heating;	100%

4,6-dichloropyrimidine (1193-21-1) + methylhydrazine (60-34-4) → 4,6-bis(1-methylhydrazino)pyrimidine (618428-20-9)

Conditions	Yield
for 2h; Heating;	100%
for 2h; Inert atmosphere; Reflux;	86%
Reflux; Inert atmosphere;

4,6-dichloropyrimidine (1193-21-1) + dimethyl amine (124-40-3) → 6-chloro-N,N-dimethylpyrimidin-4-amine (31058-83-0)

Conditions	Yield
With triethylamine In isopropyl alcohol Heating;	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 20℃; for 28h;
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;
With potassium carbonate In tetrahydrofuran; 1,4-dioxane for 14h; Reflux;
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethanol at 150℃; for 0.0833333h; Microwave irradiation;

4,6-dichloropyrimidine (1193-21-1) + tert-butyl [(3R)-pyrrolidin-3-yl]methylcarbamate (392338-15-7) → tert-butyl (R)-(1-(2-amino-6-chloropyrimidin-4-yl)pyrrolidin-3-yl)(methyl)carbamate (929716-71-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol for 24h; Product distribution / selectivity; Heating / reflux;	100%

(R)-4-[1-(4-fluorophenyl)ethyl]piperazine (862270-48-2) + 4,6-dichloropyrimidine (1193-21-1) → 4-chloro-6-{4-[(R)-1-(4-fluoro-phenyl)-ethyl]-piperazin-1-yl}-pyrimidine (1020064-27-0)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 70℃; for 6h;	100%

4,6-dichloropyrimidine (1193-21-1) + tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (144222-22-0) → tert-butyl 4-((6-chloropyrimidin-4-ylamino)methyl)-piperidine-1-carboxylate (939986-79-5)

Conditions	Yield
With potassium carbonate In acetonitrile at 120℃; for 0.5h; Microwave irradiation;	100%

4,6-dichloropyrimidine (1193-21-1) + t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) → tert-butyl 4-((6-chloropyrimidin-4-yl)oxy)piperidine-1-carboxylate (442199-19-1)

Conditions	Yield
Stage #1: t-butyl 4-hydroxy piperidine-1-carboxylate With sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 1h; Stage #2: 4,6-dichloropyrimidine In tetrahydrofuran; mineral oil at 20℃; for 2h;	100%
Stage #1: t-butyl 4-hydroxy piperidine-1-carboxylate With sodium hydride In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #2: 4,6-dichloropyrimidine In tetrahydrofuran at 20℃; for 2h;	72%
Stage #1: t-butyl 4-hydroxy piperidine-1-carboxylate With sodium hydride In tetrahydrofuran at 60℃; for 0.5h; Stage #2: 4,6-dichloropyrimidine In tetrahydrofuran at 20℃;	59%

4,6-dichloropyrimidine (1193-21-1) + 4-carboxamidopiperidine (39546-32-2) → 1-(6-chloropyrimidin-4-yl)piperidine-4-carboxamide (1242240-92-1)

Conditions	Yield
With triethylamine In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; Microwave irradiation;	100%
With triethylamine In ethanol at 100℃; for 1h; Microwave irradiation;	71%
With triethylamine Microwave irradiation;

4,6-dichloropyrimidine (1193-21-1) + 6-hydroxy-3,4-dimethyl-3H-benzoxazol-2-one (1231749-37-3) → 6-(6-chloro-pyrimidin-4-yloxy)-3,4-dimethyl-3H-benzoxazol-2-one (1231749-35-1)

Conditions	Yield
Stage #1: 6-hydroxy-3,4-dimethyl-3H-benzoxazol-2-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h; Stage #2: 4,6-dichloropyrimidine In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;	100%

4,6-dichloropyrimidine (1193-21-1) + (S)-4-methyl-2-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-6-ol (1231750-06-3) → (S)-6-(6-chloropyrimidin-4-yloxy)-4-methyl-2-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazole (1231750-08-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	100%

4,6-dichloropyrimidine (1193-21-1) + 1-Boc-amine-11-amino-3,6,9-trioxaundecane (101187-40-0) → tert-butyl {2-[2-(2-{2-[(6-chloropyrimidin-4-yl)amino]ethoxy}ethoxy)ethoxy]ethyl}carbamate

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 17h;	100%

4,6-dichloropyrimidine (1193-21-1) + 2-(7-(difluoromethoxy)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-amine hydrochloride → 6-chloro-N-(2-(7-(difluoromethoxy)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethyl)pyrimidin-4-amine

Conditions	Yield
With triethylamine In isopropyl alcohol at 95℃; for 2.5h; Inert atmosphere;	100%

4,6-dichloropyrimidine (1193-21-1) + (S)-1-(4-Fluoro-phenyl)-ethylamine (66399-30-2) → (S)-6-chloro-N-(1-(4-fluorophenyl)ethyl)pyrimidin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 50℃; for 5h;	100%

4,6-dichloropyrimidine (1193-21-1) + (1S)-1-(2,4-difluorophenyl)ethanamine (845252-02-0) → C12H10ClF2N3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 50℃;	100%

4,6-dichloropyrimidine (1193-21-1) + 1-(2-chloro-4-fluorophenyl)ethan-1-amine → C12H10Cl2FN3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 50℃;	100%

4,6-dichloropyrimidine (1193-21-1) + 1,2-diamino-benzene (95-54-5) → C10H9ClN4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 150℃; for 0.166667h; Irradiation;	100%

4,6-dichloropyrimidine (1193-21-1) + Sodium N-benzylglycinate → 6--4-chloropyrimidine (155670-20-5)

Conditions	Yield
In ethanol Heating;	99.2%

4,6-dichloropyrimidine (1193-21-1) + 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (151266-23-8) → 1-(6-chloropyrimidin-4-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions	Yield
Stage #1: 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4,6-dichloropyrimidine In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;	99.2%
Stage #1: 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4,6-dichloropyrimidine In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;	99.2%
Stage #1: 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4,6-dichloropyrimidine In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;	99.2%

4,6-dichloropyrimidine (1193-21-1) + (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride (79200-57-0) → (1R,2S,3R,5R)-3-[(6-Chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)-cyclopentane-1,2-diol (1007124-88-0)

Conditions	Yield
With triethylamine In isopropyl alcohol at 90℃; for 1h; Product distribution / selectivity;	99%
With triethylamine In ethanol at 150℃; for 0.25h; Product distribution / selectivity; Microwave irradiation;	90%

4,6-dichloropyrimidine (1193-21-1) + 3-Trifluoromethylphenol (98-17-9) → 4-chloro-6-[(α,α,α-trifluoro-m-tolyl)oxy]pyrimidine

Conditions	Yield
With potassium carbonate In acetone	99%
With potassium carbonate In acetone	99%

4,6-dichloropyrimidine (1193-21-1) + 4-fluoro-3-(trifluoromethyl)phenol (61721-07-1) → 4-chloro-6-[(α,α,α,4-tetrafluoro-m-tolyl)oxy]pyrimidine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	99%
With potassium carbonate In N,N-dimethyl-formamide	99%
With potassium carbonate In N,N-dimethyl-formamide	99%
With sodium hydroxide In water; toluene	70%

4,6-dichloropyrimidine (1193-21-1) → 6-chloroisocytosine (1194-21-4)

Conditions	Yield
With acetic acid In sodium hydroxide	99%

4,6-dichloropyrimidine (1193-21-1) + isobutylamine (78-81-9) → 4-isobutylamino-6-chloropyrimidine (1220028-08-9)

Conditions	Yield
In methanol at 20℃; for 6.16667h; Cooling with ice;	99%

4,6-dichloropyrimidine (1193-21-1) + 4-Aminobiphenyl (92-67-1) → N-([1,1'-biphenyl]-4-yl)-6-chloropyrimidin-4-amine

Conditions	Yield
With triethylamine In ethanol at 120℃; for 3h;	99%

pyrrolidine (123-75-1) + 4,6-dichloropyrimidine (1193-21-1) → 4-Chloro-6-(pyrrolidin-1-yl)pyrimidine (939986-64-8)

Conditions	Yield
With triethylamine In isopropyl alcohol Heating;	98%
With triethylamine In ethanol at 20℃; for 0.25h;	63%
In isopropyl alcohol Reflux;

4,6-dichloropyrimidine (1193-21-1) + t-butoxycarbonylhydrazine (870-46-2) → tert-butyl N-[(6-chloropyrimidin-4-yl)amino]carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux;	98%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 68h; Reflux;	98%
With N-ethyl-N,N-diisopropylamine In ethanol at 120℃; for 1h;

4,6-dichloropyrimidine (1193-21-1) + D-phenylalanine methyl ester hydrochloride (13033-84-6) → methyl (2R)-2-[(6-chloropyrimidin-4-yl)amino]-3-phenylpropanoate (693792-77-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 80℃;	98%

4,6-dichloropyrimidine (1193-21-1) + 6-(2-methyl-5-nitrophenyl)-1H-indole (1298084-34-0) → 1-(6-chloropyrimidine-4-yl)-6-(2-methyl-5-nitrophenyl)-1H-indole (1298084-35-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil	98%

Upstream product

• 75-44-5 phosgene 
• 1193-24-4 4,6-pyrimidinediol 
• 791-28-6 Triphenylphosphine oxide 
• 2526-64-9 dichlorotriphenylphosphorane 
• 89283-48-7 4-chloro-6-methylsulfanylpyrimidine 
• 2434-56-2 4,6-diaminopyrimidine 
• 288-32-4 1H-imidazole 
• 1122-58-3 dmap 
• 104-90-5 5-ethyl-2-methyl-pyridine 
• 26452-81-3 4-chloro-6-methoxy-pyrimidine 
• 25600-32-2 aminoketone hydrochloride 
• 13507-15-8 acetamide hydrochloride 
• 623-49-4 ethyl cyanoformate 
• 75-05-8 acetonitrile 

Downstream Products

• 19646-06-1 4,6-diiodopyrimidine 
• 258506-74-0 4-chloro-6-iodopyrimidine 
• 750559-62-7 4-(6-chloro-pyrimidin-4-yl)-benzoic acid 
• 169677-46-7 4-tert-butyl-N-(6-chloro-4-pyrimidinyl)benzenesulfonamide 
• 36847-10-6 4,6-dibromopyrimidine 
• 263276-29-5 4-chloro-6-propylthio-pyrimidine 
• 302964-27-8 2-(6-chloro-pyrimidin-4-ylamino)-thiazole-5-carboxylic acid (2-chloro-6-methyl-phenyl)-amide 
• 334893-17-3 6-chloro-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine 
• 26452-81-3 4-chloro-6-methoxy-pyrimidine 
• 405939-02-8 (3-chlorophenyl)(6-chloropyrimidin-4-yl)amine 
• 915069-51-1 4-chloro-6-(3-nitrophenyl)-pyrimidine 
• 75634-03-6 4-chloro-6-(2-methoxy-phenyl)-pyrimidine 
• 872510-82-2 (6-chloro-pyrimidin-4-yl)-(3-trifluoromethyl-phenyl)-amine 

Relevant articles and documents

The efficient one-step chlorination of methylsulfanyl group on pyrimidine ring system with sulfuryl chloride

A facile one-step transformation of methylsulfanyl and arylsulfanyl groups on pyrimidine ring system into the corresponding chloride group was achieved using sulfuryl chloride in acetonitrile/dichloromethane.

4,6-dichloropyrimidine preparation method

The invention discloses a 4,6-dichloropyrimidine preparation method, which comprises: carrying out a cyclization reaction on a compound represented by a formula I and malononitrile in a sodium alcoholate system, evaporating to remove the alcohol after the cyclization reaction, adding water to dissolve, regulating the pH value with an acid, and carrying out cooling crystallization to obtain a compound represented by a formula II, wherein in the compound represented by a formula I, X is HCl, HNO3, H2SO4 or acetic acid; and adding hydrochloric acid and sodium nitrite into the compound representedby the formula II, carrying out a diazotization reaction, carrying out a Sandmeyer reaction under catalysis, extracting with a polar solvent after the reaction, and distilling to obtain a compound represented by a formula III, ie., 4,6-dichloropyrimidine.

Preparation method of 4, 6-dichloropyrimidine

The invention discloses a preparation method of 4, 6-dichloropyrimidine, which comprises the following steps: (1) dissolving 4, 6-dihydroxypyrimidine and a catalyst in a polar solvent, and mixing to obtain a mixed solution containing 4, 6-dihydroxypyrimidine; (2) adding chlorine or liquid chlorine into the mixed solution, and reacting to obtain a mixed solution containing 4, 6-dichloropyrimidine;(3) distilling the mixed solution containing 4, 6-dichloropyrimidine to remove the solvent, deacidifying, and distilling to recover byproduct phosphorus oxychloride, thereby obtaining a 4, 6-dichloropyrimidine crude product; (5) carrying out extraction separation on the 4, 6-dichloropyrimidine crude product, carrying out flash evaporation to remove a solvent and leave 4, 6-dichloropyrimidine in awater phase; and cooling and crystallizing the water phase, and carrying out dehydration treatment to obtain the 4, 6-dichloropyrimidine product. According to the method, the low-price easily-available catalyst is adopted, so that the reaction efficiency can be remarkably improved; chlorine/liquid chlorine is used as a chlorinating agent, so that the risk of the process is greatly reduced, and thebyproduct phosphorus oxychloride with high additional value is produced.

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Synthesis process 4,6-dichloropyrimidine (by machine translation)

The invention provides a method 4,6 - for synthesizing,dichloropyrimidine as the raw material, with,hydroxypyrimidine as the reaction, 4,6 -dimethylaniline is used as the reaction, and the part of wastewater generated by,dimethylaniline in the finally produced wastewater N,N - according to the present invention is not limited to the consumption amount of the.dichloropyrimidine product produced by the invention, as a raw material. 4,6 - The present invention provides a method for producing waste water, by rectification in a manner of rectifying the product by distillation in a manner of rectifying, the product by a rectification method according to the present invention as a raw material solution, and a, solvent; in 1kg4,6 - a solvent; according to the present invention as a raw material of the present 6 - 7kg, invention in the present invention. (by machine translation)

Design, synthesis, and anticancer evaluation of acetamide and hydrazine analogues of pyrimidine

A library of acetamide and hydrazine analogues were generated on the pyrimidine ring through a multistep reaction starting from 5-nitro-pyrimidine-4,6-diol and pyrimidine-4,6-diol, respectively. The synthesized analogues were screened for in vitro cytotoxic activity against various human cancer cell lines like HCT-1 and HT-15 (colon), MCF-7(breast), PC-3 (prostrate), SF268 (CNS) using MTT method. From the bioassay results, it was observed that even though many of the synthesized derivatives exhibited a good potency against various screened cancer cell lines, compound 14a from the acetamide series was found to show potent anticancer activity on all the tested cancer cell lines with IC50 value of 0.36μM on CNS cell line and 1.6μM on HT-21 cell line, and compound 19xxi from hydrazine series of pyrimidine showed potent activity against three tested cancer cell lines with IC50 value of 0.76μM on HT-29 cell line, 2.6μM on HCT-15, and 3.2μM on MCF-7 cell line.

Pyrimidine hydrazone derivative and preparation method and application thereof

The invention relates to pyrimidine hydrazone derivatives as shown in a chemical structural formula I or II, pharmaceutically acceptable salts and pharmaceutical compositions thereof, and an application of the pyrimidine hydrazone derivatives and the pharmaceutically acceptable salts and the pharmaceutical compositions in preparation of influenza virus neuraminidase inhibitors, wherein X is selected from: fluorine, chlorine, bromine, hydroxyl, dihydroxy, 2-hydroxy-3-methoxy, 2-hydroxy-4-methoxy, 2-hydroxy-5-C1-C2 alkoxy, 2-hydroxy-6-C1-C2 alkoxy, 3-hydroxy-2-C1-C2 alkoxy, 3-hydroxy-4-C1-C2 alkoxy, 3-hydroxy-5-methyl C1-C2 alkoxy , 3-hydroxy-6-C1-C2 alkoxy, 4-hydroxy-2-C1-C2 alkoxy, 4-hydroxy-3-C1-C2 alkoxy, 4-hydroxy-3, 5-diC1-C2 alkoxy, trihydroxy or 4-hydroxy-3,5-dimethyl; and Y is selected from: fluorine, chlorine, bromine, acetamido, hydroxyl or methoxy.

Preparation method and application of 4, 6-dichloropyrimidine

The invention discloses a preparation method and application of 4, 6-dichloropyrimidine, and belongs to the technical field of chemical engineering. The structural formula of the 4, 6-dichloropyrimidine is C4H2Cl2N2, the molecular weight of the 4, 6-dichloropyrimidine is 148.98, and the 4, 6-dichloropyrimidine is light yellow to white crystals. The preparation method of the 4, 6-dichloropyrimidinecomprises the following steps of: mixing an organic phosphorus compound, phosphorus pentachloride and 4, 6-dihydroxypyrimidine in an organic solvent, controlling the temperature to be 120DEG C, and carrying out reaction for a certain time to obtain a mixed solution containing 4, 6-dichloropyrimidine and phosphorus oxychloride; cooling the mixed solution containing 4, 6-dichloropyrimidine and phosphorus oxychloride to room temperature, and performing extracting to obtain an organic phase; washing and concentrating the organic phase, and then conducting cooling and crystallizing to obtain pure4, 6-dichloropyrimidine. The method provided by the invention is easy to control in operation and good in safety, and after extraction, the catalyst and the phosphorus-containing by-product are not damaged and can be recycled, so that possibility is provided for comprehensive utilization of the phosphorus-containing by-product, and environmental pollution is avoided.

Preparation method of chloro-substituted polyhydroxy aza-aromatic ring compound (by machine translation)

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)

In the stripping column in the application of the dichloro pyrimidine purification (by machine translation)

The present invention provides a pure aliphatic chloro pyrimidine of stripping method, comprises the following steps: A) dihydroxy pyrimidine carried out after the chlorination reaction, to obtain dichloro pyrimidine reaction mixed solution; B) reaction mixed solution adding water hydrolysis, or by adding ice water to ice solution, then the organic solvent extraction, including two chlorine pyrimidine crude product obtained organic phase; C) containing dichloro pyrimidine crude organic phase is the top or upper part enters the stripping column, or the lower part of the water vapor from the bottom of the stripping column, containing two chloro pyrimidine crude organic phase flushes steams, including two chlorine pyrimidine pure product obtained organic phase; D) organic phase containing dichloro pyrimidine pure product, reduced pressure or normal pressure distillation concentrated, the temperature crystallization, centrifugation or filtration to obtain two chloro pyrimidine pure product. This invention adopts the reverse steam stripping column, two chloro pyrimidine crude to drip or spray mode, the state of the droplet, direct contact with water vapor, so that the purification efficiency, refining yield is greatly improved, and is suitable for industrial production and application. (by machine translation)