32779-36-5

Basic information

• Product Name: 5-Bromo-2-chloropyrimidine
• Synonyms: PYRIMIDINE, 5-BROMO-2-CHLORO-;2-CHLORO-5-BROMOPYRIMIDINE;2C5BP;5-BROMO-2-CHLOROPYRIMIDINE;5-BROMO-2-CHLOROPYRIMIDNE;5-BROMO-2-CHLOROPYRIMIDINE(MINIMUM85%);MAJORIMPURITYIS2,5-DIBROMOPYRIMIDINE ;5-BROMO-2-CHLOROPYRIMIDINE(MINIMUM95%)
• CAS NO: 32779-36-5
• Molecular Formula: C₄H₂BrClN₂
• Molecular Weight: 193.43
• EINECS: -0
• Product Categories: Pyrimidine Series;Halides;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Pyrazines, Pyrimidines & Pyridazines;Pyrimidine;Halogenated;Organohalides;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Variety of halogenated heterocyclic series;Building Blocks;C4 to C5;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series;Pharmaceutical intermediates;Thiophenes
• Mol File: 32779-36-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 76-81 °C(lit.)
• Boiling Point: 95°C 15mm
• Flash Point: 95°C/15mm
• Appearance: Off-white to beige/Crystalline Powder
• Density: 1.86 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -2.84±0.22(Predicted)
• Water Solubility: insoluble
• BRN: 507955
• CAS DataBase Reference: 5-Bromo-2-chloropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-chloropyrimidine(32779-36-5)
• EPA Substance Registry System: 5-Bromo-2-chloropyrimidine(32779-36-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/39-37/39-36
• RIDADR: UN 3335
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 32779-36-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to beige crystalline powder

Uses

Different sources of media describe the Uses of 32779-36-5 differently. You can refer to the following data:
1. 5-Bromo-2-chloropyrimidine is a intermediate in the synthesis of pharmaceutical goods such as inhibitors.
2. It is applied as a pharmaceutical intermediate, in the synthesis of pharmaceutical goods such as inhibitors. It is also employed in the cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines.

InChI:InChI=1/C4H2BrClN2/c5-3-1-7-4(6)8-2-3/h1-2H

Synthetic route

5-bromopyrimidin-2-ol (38353-06-9) → 5-Bromo-2-chloropyrimidine (32779-36-5)

Conditions	Yield
With trichlorophosphate at 80℃;	88%
With trichlorophosphate In N,N-dimethyl-aniline for 4h; Heating / reflux;	75%
With N,N-dimethyl-aniline; trichlorophosphate for 4h; Heating;	73%

5-bromo-1H-pyrimidin-2-one (38353-06-9) → 5-Bromo-2-chloropyrimidine (32779-36-5)

Conditions	Yield
With N,N-dimethyl-aniline; trichlorophosphate for 6h; Heating / reflux;	84%

5-bromopyrimidine (4595-59-9) → 5-Bromo-2-chloropyrimidine (32779-36-5)

Conditions	Yield
With trichlorophosphate at 0 - 120℃; for 4.16667h;	80%
With trichlorophosphate at 0 - 120℃; for 4.25h;

5-bromo-2-hydroxypyrimidine → 5-Bromo-2-chloropyrimidine (32779-36-5)

Conditions	Yield
With N,N-dimethyl-aniline; trichlorophosphate	77%

5-bromo-2-aminopyrimidine (7752-82-1) → 5-Bromo-2-chloropyrimidine (32779-36-5)

Conditions	Yield
With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 20℃; Inert atmosphere;	36%

4-amino-5-bromo-2-chloropyrimidine (205672-25-9) → 5-Bromo-2-chloropyrimidine (32779-36-5)

Conditions	Yield
With tetrahydrofuran; tert.-butylnitrite; dimethyl sulfoxide at 30℃; for 2h; Green chemistry;	27%

2-chloropyrimidine (1722-12-9) → 5-Bromo-2-chloropyrimidine (32779-36-5)

Conditions	Yield
With N-Bromosuccinimide; boron trifluoride diethyl etherate In acetonitrile at 20℃; Solvent; Reflux;	14.1 g
With bromine; acetic acid Reflux;	29 g
With bromine; acetic acid Reflux;	29 g

5-Bromo-2-chloropyrimidine (32779-36-5) + methylamine (74-89-5) → 5-bromo-N-methylpyrimidin-2-amine (31402-54-7)

Conditions	Yield
In methanol; water for 72h; Reflux;	100%
With potassium carbonate In tetrahydrofuran; water; tert-butyl alcohol at 150℃; for 0.25h; microwave;	98%
Stage #1: 5-Bromo-2-chloropyrimidine; methylamine In methanol at 115℃; for 48h; Sealed vessel; Stage #2: With sodium hydroxide In dichloromethane; water	93%

5-Bromo-2-chloropyrimidine (32779-36-5) + isopropyl alcohol (67-63-0) → 5-bromo-2-(propan-2-yloxy)pyrimidine (121487-12-5)

Conditions	Yield
With sodium at 20℃;	100%
Stage #1: isopropyl alcohol With sodium hydride Stage #2: 5-Bromo-2-chloropyrimidine for 15h; Reflux;
With sodium hydride at 60℃; for 24.5h; Heating / reflux;

morpholine (110-91-8) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 4-(5-bromopyrimidin-2-yl)morpholine (84539-22-0)

Conditions	Yield
Stage #1: morpholine With potassium carbonate In acetonitrile at 20℃; for 1h; Stage #2: 5-Bromo-2-chloropyrimidine In acetonitrile for 18h; Reflux;	100%
With potassium carbonate In acetonitrile at 85℃; for 10h;	95%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h;	85%

2-chloro-4-methoxyphenol (18113-03-6) + 5-Bromo-2-chloropyrimidine (32779-36-5) → C11H8BrClN2O2

Conditions	Yield
With potassium carbonate In butanone at 100℃; for 5h;	100%

N-Boc-1,3-diaminopropane (75178-96-0) + 5-Bromo-2-chloropyrimidine (32779-36-5) → tert-butyl (3-((5-bromopyrimidin-2-yl)amino)propyl)carbamate

Conditions	Yield
In ethanol for 6h; Reflux;	100%
With triethylamine In ethanol at 80℃; for 4h; Sealed tube;

1-methyl-piperazine (109-01-3) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 2-chloro-5-(4-methylpiperazin-1-yl)pyrimidine

Conditions	Yield
In 1,4-dioxane for 2h; Reflux;	100%

5-Bromo-2-chloropyrimidine (32779-36-5) + sodium thiomethoxide (5188-07-8) → 2,5-dimethylthiopyrimidine

Conditions	Yield
In N,N-dimethyl-formamide at 25 - 40℃; for 3h; Temperature; Inert atmosphere;	100%

5-Bromo-2-chloropyrimidine (32779-36-5) + 1-[3-(trifluoromethoxy)phenyl]methanamine (93071-75-1) → 5-bromo-N-{[3-(trifluoromethoxy)phenyl]methyl}pyrimidin-2-amine

Conditions	Yield
With diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 48h;	99.6%

4-HYDROXYPIPERIDINE (5382-16-1) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 1-(5-bromopyrimidin-2-yl)-4-piperidinol (887425-47-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 15h; Heating / reflux;	99%
With triethylamine In N,N-dimethyl-formamide at 100℃; for 16h;	97.7%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 0.0833333h; Microwave;
With triethylamine In ethanol at 90℃; for 0.5h;

tert-butyl 4-(piperazinylsulfonyl)-perhydro-2H-pyran-4-carboxylate (622387-56-8) + 5-Bromo-2-chloropyrimidine (32779-36-5) → tert-butyl 4-{[4-(5-bromopyrimidin-2-yl)piperazin-1-yl]sulfonyl}tetrahydro-2H-pyran-4-carboxylate (622386-44-1)

Conditions	Yield
With triethylamine In toluene for 18h; Heating / reflux;	99%

sodium cyanide (143-33-9) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 5-bromopyrimidine-2-carbonitrile (38275-57-9)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In water; dimethyl sulfoxide at 20℃; for 18h;	99%
1,4-diaza-bicyclo[2.2.2]octane In water; dimethyl sulfoxide at 20℃;	88%
With 1,4-diaza-bicyclo[2.2.2]octane In water; dimethyl sulfoxide at 20℃; for 2h;
In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;

5-Bromo-2-chloropyrimidine (32779-36-5) + (R)-tert-butyl 3-methylpiperazine-1-carboxylate (163765-44-4) → (R)-tert-butyl 4-(5-bromopyrimidin-2-yl)-3-methylpiperazine-1-carboxylate (1272973-68-8)

Conditions	Yield
With potassium carbonate In propyl cyanide at 120℃; for 15h;	99%
With potassium carbonate In acetonitrile at 150℃; for 1h;	73%

2,4-difluorobenzyl alcohol (56456-47-4) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 5-bromo-2-(2,4-difluorobenzyloxy)pyrimidine

Conditions	Yield
Stage #1: 2,4-difluorobenzyl alcohol With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 5-Bromo-2-chloropyrimidine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; Inert atmosphere;	99%

5-Bromo-2-chloropyrimidine (32779-36-5) + benzyl-methyl-amine (103-67-3) → N-benzyl-5-bromo-N-methylpyrimidin-2-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 100℃; for 2h;	99%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 100℃; for 2h;	99%

3-monochlorophenol (108-43-0) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 5-bromo-2-(3-chlorophenoxy)pyrimidine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	99%

5-Bromo-2-chloropyrimidine (32779-36-5) + 1-amino-3-(dimethylamino)propane (109-55-7) → N1-(5-bromopyrimidin-2-yl)-N3,N3-dimethylpropane-1,3-diamine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 1h;	99%

ethanol (64-17-5) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 2-chloro-5-ethoxypyrimidine (82153-68-2)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In toluene at 100℃; for 3h;	98.6%

5-Bromo-2-chloropyrimidine (32779-36-5) + benzyl alcohol (100-51-6) → 2-(benzyloxy)-5-bromopyrimidine (742058-39-5)

Conditions	Yield
Stage #1: benzyl alcohol With sodium hydride In tetrahydrofuran for 0.166667h; Stage #2: 5-Bromo-2-chloropyrimidine In tetrahydrofuran at 20℃; Stirring overnight;	98%
Stage #1: benzyl alcohol With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 5-Bromo-2-chloropyrimidine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; Inert atmosphere;	97%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1.5h;
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 2h;	10.2 g

5-Bromo-2-chloropyrimidine (32779-36-5) + Benzo[b]thiophene (95-15-8) → 4-(benzo[b]thiophen-2-yl)-5-bromo-2-chloropyrimidine

Conditions	Yield
Stage #1: Benzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: 5-Bromo-2-chloropyrimidine In tetrahydrofuran; hexane at -30 - 0℃; for 1h; Stage #3: With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone more than 3 stages;	98%
Stage #1: Benzo[b]thiophene With n-butyllithium In diethyl ether; hexane at 0℃; for 2.75h; Stage #2: 5-Bromo-2-chloropyrimidine In tetrahydrofuran; diethyl ether; hexane at -78℃; for 1.75h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; methanol; diethyl ether; hexane at -24 - -15℃;	62%

5-Bromo-2-chloropyrimidine (32779-36-5) + 4-methoxy-benzylamine (2393-23-9) → (5-bromo-pyrimidin-2-yl)-(4-methoxy-benzyl)-amine (859207-02-6)

Conditions	Yield
at 120℃; for 2h;	98%
at 120℃; for 2h;	98%
at 120℃; for 2h;	98%

cyanoacetic acid tert-butyl ester (1116-98-9) + 5-Bromo-2-chloropyrimidine (32779-36-5) → tert-butyl 2-(5-bromopyrimidin-2-yl)-2-cyanoacetic acid (1305329-97-8)

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 5-Bromo-2-chloropyrimidine In tetrahydrofuran at 20℃; for 18h;	98%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	35.72%

5-Bromo-2-chloropyrimidine (32779-36-5) + para-Chlorobenzyl alcohol (873-76-7) → 5-bromo-2-(4-chlorobenzyloxy)pyrimidine

Conditions	Yield
Stage #1: para-Chlorobenzyl alcohol With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 5-Bromo-2-chloropyrimidine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; Inert atmosphere;	98%

hexamethylene imine (111-49-9) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 1-(5-bromopyrimidin-2-yl)azepane (1015241-96-9)

Conditions	Yield
In dichloromethane at 20℃; for 2h;	98%
In dichloromethane at 20℃; for 2h; Schlenk technique; Inert atmosphere;	98%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere;	94%
With N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 150℃; for 0.5h; Microwave irradiation;	91%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h;	90%

ethylene glycol (107-21-1) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 2-((5-bromopyrimidin-2-yl)oxy)ethan-1-ol (1246922-88-2)

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 45℃; for 8h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	98%

benzoimidazole (51-17-2) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 1-(5-bromopyrimidin-2-yl)-1H-benzo[d]imidazole (883230-69-1)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 70℃; for 24h; Inert atmosphere;	97%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃;

5-Bromo-2-chloropyrimidine (32779-36-5) + dimethyl amine (124-40-3) → 5-bromo-N,N-dimethylpyrimidin-2-amine (38696-21-8)

Conditions	Yield
In ethanol at 115℃; for 48h;	97%
In tetrahydrofuran at 20℃; Inert atmosphere;	86%
In tetrahydrofuran; acetonitrile at 20℃; for 1h;	3.2 g
With potassium carbonate In methanol at 20℃; for 1h;

(S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol (187235-08-1) + 5-Bromo-2-chloropyrimidine (32779-36-5) → (S)‐6‐((5‐bromopyrimidin‐2‐yl)oxy)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazine (1188328-31-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; chemoselective reaction;	97%

5-Bromo-2-chloropyrimidine (32779-36-5) + trifluoroacetic acid (76-05-1) → (2-chloropyrimidin-5-yl-1-ium)boronic acid trifluoroacetate

Conditions	Yield
Stage #1: 5-Bromo-2-chloropyrimidine With n-butyllithium; Triisopropyl borate In tetrahydrofuran; toluene at -78℃; for 1.83333h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at -78℃; Stage #3: trifluoroacetic acid In water; acetonitrile HPLC;	97%

3-fluoro-benzenemethanol (456-47-3) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 5-bromo-2-(3-fluorobenzyloxy)pyrimidine

Conditions	Yield
Stage #1: 3-fluoro-benzenemethanol With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 5-Bromo-2-chloropyrimidine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; Inert atmosphere;	97%

N-(3-chloro-4-hydroxyphenyl)carbamic acid tert-butyl ester (911297-03-5) + 5-Bromo-2-chloropyrimidine (32779-36-5) → C15H15BrClN3O3

Conditions	Yield
With potassium carbonate In butanone at 100℃; for 4h;	97%

Upstream product

• 205672-25-9 4-amino-5-bromo-2-chloropyrimidine 
• 1722-12-9 2-chloropyrimidine 
• 4595-59-9 5-bromopyrimidine 
• 38353-06-9 5-bromo-1H-pyrimidin-2-one 
• 38353-06-9 5-bromopyrimidin-2-ol 
• 7752-82-1 5-bromo-2-aminopyrimidine 

Downstream Products

• 73267-74-0 5-Bromo-2-(2-methylphenoxy)pyrimidine 
• 22536-61-4 2-chloro-5-methylpyrimidine 
• 1722-12-9 2-chloropyrimidine 
• 111196-81-7 2-chloro-5-ethylpyrimidine 
• 76660-37-2 4-((5-bromopyrimidin-2-yl)oxy)aniline 
• 849035-61-6 4-(5-bromopyrimidin-2-ylsulfanyl)phenylamine 
• 910547-32-9 2,5-bis-(4-cyanophenyl)-pyrimidine 
• 706811-18-9 2-methoxy-ethanesulfamic acid [6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-amide 
• 706811-19-0 2-methoxyethanesulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}-amide 
• 870096-77-8 C₁₅H₁₇BrN₄O₂ 
• 870096-76-7 N-(5-bromo-pyrimidin-2-yl)-benzene-1,3-diamine 
• 617703-45-4 5-bromo-2-(2-pyrrolidin-1-yl-ethoxy)-pyrimidine 
• 346671-88-3 4-tert.-butyl-N-[6-(4-(5-bromo-2-pyrimidinyloxy)-2-butynyloxy)-5-(o-methoxy-phenoxy)-4-pyrimidinyl]-benzene sulfonamide 
• 346671-93-0 4-tert.-butyl-N-[6-(4-(5-bromo-2-pyrimidinyloxy)-2-butynyloxy)-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-benzene sulfonamide 

Relevant articles and documents

Preparation method 2 - methyl -5 -bromopyrimidine

The invention specifically discloses a preparation method of 2 - methyl -5 -bromopyrimidine, and belongs to the technical field of organic synthesis. The method comprises the following steps: a) taking 2 - amino -5 -bromopyrimidine as a raw material, carrying out diazotization reaction or Schedman reaction or 2 - hydroxyl -5 -bromopyrimidine as a raw material to obtain 2 -halo -5 -bromopyrimidine through a halogenated reagent. b) The carboxylic diester is substituted with 2 - halo -5 - bromopyrimidine to give 2-position substituted product. c) The last 2 -bit substituted product is reacted under basic, high temperature conditions to give 2 - methyl -5 - bromopyrimidine. The method has the advantages of easily available raw materials, low cost, simple flow and potential industrial amplification prospect.

Preparation method for 2-chloro-5-(piperidin-4-yl)pyrimidine

The invention discloses a preparation method for 2-chloro-5-(piperidin-4-yl)pyrimidine. The target product is obtained by using 2-chloropyrimidine as a starting raw material, performing a brominationreaction, performing a coupling reaction, performing an elimination reaction and performing a catalytic hydrogenation reaction. The compound provided by the invention is an important pharmaceutical intermediate.

Preparation of 2-amino-pyrimidine-5-boronic acid frequency that ester method

A method of preparing 2-aminopyrimidine-5-boronic acid pinacol ester is disclosed. The method includes subjecting 2-chloropyrimidine that is a raw material and NBS to bromization under catalysis of BF3-Et2O to obtain 2-chloro-5-bromopyrimidine; reacting the 2-chloro-5-bromopyrimidine with n-Bu3MgLi at a temperature ranging from -20 DEG C to -10 DEG C; adding methoxyboronic acid pinacol ester or isopropoxyboronic acid pinacol ester; performing boronization to obtain 2-chloropyrimidine-5-boronic acid pinacol ester; adding into ammonia water or a methanol-ammonia solution; and reacting at 80-100 DEG C in a sealed manner to obtain the 2-chloropyrimidine-5-boronic acid pinacol ester. Synthetic process conditions of the method are mild. An ultralow-temperature reaction is avoided. Reactions can be performed continuously. A pure product can be obtained only by simple recrystallization of the final product.