6840-45-5

Usage

InChI:InChI=1/C6H4BrN3/c7-5-4-9-6-8-2-1-3-10(5)6/h1-4H

Synthetic route

imidazo[1,2-a]pyrimidine (274-95-3) → 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5)

Conditions	Yield
With N-Bromosuccinimide In chloroform for 12h; Heating;
With bromine; sodium acetate In methanol at -10℃;	3.2 g

N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (1112983-31-9) + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → N-(2-chloro-5-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (1246184-45-1)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; for 5h;	58%

tert-butyl 2-(3-carbamoyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)acetate + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → tert-butyl 2-(3-carbamoyl-5-(imidazo[1,2-a]pyrimidin-3-yl)-1H-indol-1-yl)acetate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; acetonitrile at 80℃; for 16h; Inert atmosphere;	51.2%

4-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)pyridin-2-amine + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 4-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-2-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere; Sealed tube;	51%

5-ethynyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)nicotinamide + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 5-(imidazo[1,2-a]pyrimidin-3-ylethynyl)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)nicotinamide

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 15h; Inert atmosphere;	29.3%

3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → N-[6-(imidazo[1,2-a]pyrimidin-3-ylsulphonyl)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (1205125-07-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 190 °C / sealed tube; Microwave irradiation 2: pyridine / ethyl acetate / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 180 °C / sealed tube 2.1: hydrogenchloride; water / ethanol / 8 h / Reflux 3.1: acetic acid 3.2: 48 h / 20 °C 3.3: pH 11 4.1: pyridine / ethyl acetate / 16 h / 20 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C View Scheme

3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) + 4-acetamidothiophenol (1126-81-4) → N-[4-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)phenyl]acetamide (1205121-73-8)

Conditions	Yield
With potassium carbonate In water; dimethyl sulfoxide at 180℃; for 0.2h; sealed tube;

3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → N-[6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]-3-(pyrrolidin-1-yl)propanamide (1205125-10-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 190 °C / sealed tube; Microwave irradiation 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 72 h / 20 - 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 180 °C / sealed tube 2.1: hydrogenchloride; water / ethanol / 8 h / Reflux 3.1: acetic acid 3.2: 48 h / 20 °C 3.3: pH 11 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 72 h / 20 - 50 °C View Scheme

3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 2-(4-cyclopropylpiperazin-1-yl)-N-[6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]acetamide (1205125-23-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 190 °C / sealed tube; Microwave irradiation 2: hydrogenchloride / diethyl ether / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 180 °C / sealed tube 2.1: hydrogenchloride; water / ethanol / 8 h / Reflux 3.1: acetic acid 3.2: 48 h / 20 °C 3.3: pH 11 4.1: hydrogenchloride / diethyl ether / 20 °C View Scheme

3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → (1R,2R)-N-[6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]-2-(morpholin-4-ylmethyl)cyclopropanecarboxamide (1205125-20-7) + (1S,2S)-N-[6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]-2-(morpholin-4-ylmethyl)cyclopropanecarboxamide (1205125-19-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 190 °C / sealed tube; Microwave irradiation 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / water; dimethyl sulfoxide / 0.2 h / 180 °C / sealed tube 2.1: hydrogenchloride; water / ethanol / 8 h / Reflux 3.1: acetic acid 3.2: 48 h / 20 °C 3.3: pH 11 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine View Scheme

1-(2-morpholin-4-ylethyl)-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea (1116743-47-5) + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-amine (1205121-71-6)

Conditions	Yield
With potassium carbonate In water; dimethyl sulfoxide at 190℃; for 0.2h; sealed tube; Microwave irradiation;

1-(2-morpholin-4-ylethyl)-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea (1116743-47-5) + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 1-[6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]-3-[2-(morpholin-4-yl)ethyl]urea (1205121-76-1)

Conditions	Yield
With potassium dihydrogenphosphate; triethylamine In ethanol; water for 16h; Reflux;

N-[5-fluoro-6-sulphanyl-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (1205125-27-4) + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → N-[5-fluoro-6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (1205125-26-3)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 185℃; for 0.2h; sealed tube; Microwave irradiation;

2-amino-5-fluoro-1,3-benzothiazole-6-thiol (1205125-31-0) + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 5-fluoro-6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzo-thiazol-2-amine (1205125-30-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 160℃; for 0.5h; sealed tube;

3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 3-ethynylimidazo[1,2-a]pyrimidine

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 20 h / Reflux; Inert atmosphere 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere View Scheme

3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → C29H28F3N9O (1407999-84-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 20 h / Reflux; Inert atmosphere 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 90 °C View Scheme

2-aminopyridine-5-boronic acid pinacol ester (827614-64-2) + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 5-imidazo[1,2-a]pyrimidin-3-ylpyridin-2-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 95℃; for 12h; Inert atmosphere;

5-(2-(benzylthio)-6-bromophenyl)-1H-tetrazole + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) + p-methoxybenzyl chloride (824-94-2) → C37H34N8O5S + C37H34N8O5S

Conditions	Yield
Stage #1: 5-(2-(benzylthio)-6-bromophenyl)-1H-tetrazole; p-methoxybenzyl chloride With tetrabutyl-ammonium chloride; potassium carbonate In chloroform; water at 15 - 50℃; for 3h; Stage #2: With sulfuryl dichloride; acetic acid In dichloromethane; water at 0 - 20℃; for 4h; Stage #3: 3-bromoimidazo[1,2-a]pyrimidine; p-methoxybenzyl chloride Further stages;
Stage #1: 5-(2-(benzylthio)-6-bromophenyl)-1H-tetrazole; p-methoxybenzyl chloride With tetrabutyl-ammonium chloride; potassium carbonate In chloroform; water at 15 - 50℃; for 3h; Stage #2: With sulfuryl dichloride; acetic acid In dichloromethane; water at 0 - 20℃; for 4h; Stage #3: 3-bromoimidazo[1,2-a]pyrimidine; p-methoxybenzyl chloride Further stages;

5-(2-(benzylthio)-6-bromophenyl)-1H-tetrazole + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → 3-imidazo[1,2-a]pyrimidin-3-yl-2-(1H-tetrazol-5-yl)benzenesulfonamide

Conditions	Yield
Stage #1: 5-(2-(benzylthio)-6-bromophenyl)-1H-tetrazole With tetrabutyl-ammonium chloride; potassium carbonate; p-methoxybenzyl chloride In chloroform; water at 15 - 50℃; for 3h; Stage #2: With sulfuryl dichloride; acetic acid In dichloromethane; water at 0 - 20℃; for 4h; Stage #3: 3-bromoimidazo[1,2-a]pyrimidine Further stages;
Stage #1: 5-(2-(benzylthio)-6-bromophenyl)-1H-tetrazole With tetrabutyl-ammonium chloride; potassium carbonate; p-methoxybenzyl chloride In chloroform; water at 15 - 50℃; for 3h; Stage #2: With sulfuryl dichloride; acetic acid In dichloromethane; water at 0 - 20℃; for 4h; Stage #3: 3-bromoimidazo[1,2-a]pyrimidine Further stages;

tert-butyl 2-(3-acetyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)acetate + 3-bromoimidazo[1,2-a]pyrimidine (6840-45-5) → tert-butyl 2-(3-acetyl-5-(imidazo[1,2-a]pyrimidin-3-yl)-1H-indazol-1-yl)acetate

Conditions	Yield
With caesium carbonate In water; N,N-dimethyl-formamide at 20 - 80℃; for 3h; Reagent/catalyst; Inert atmosphere;

Upstream product

• 274-95-3 imidazo[1,2-a]pyrimidine 

Downstream Products

• 1407999-84-1 C₂₉H₂₈F₃N₉O 
• 1205121-73-8 N-[4-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)phenyl]acetamide 
• 1205125-03-6 phenyl [6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]carbamate 
• 1205121-72-7 4-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)aniline 
• 1246184-45-1 N-(2-chloro-5-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide 

Relevant academic research and scientific papers

Organic compound comprising pyrimidine and organic electroluminescent device comprising the same

The present invention relates to an organic aromatic organic compound containing pyridine, and an organic electroluminescent device using the same, wherein the compound may be used as thermally activated delayed fluorescent (TADF) material due to having little energy difference between an excited singlet state and an excited triplet state. Further, the compound of the present invention may be used in an organic light-emitting diode to improve efficiency of the organic light-emitting diode and lower driving voltage thereof.COPYRIGHT KIPO 2017

Synthesis and antibacterial activity of some imidazo[1,2-a[pyrimidine derivatives

A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The 'in vitro' antibacterial activity of these compounds and their corresponding α-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobial activity.

Antifungal activity in vitro of some imidazopyrimidine derivatives

In regard to fungicidal activity of imidazole ring found in chemical compounds such as econazole, a series of 42 diversely substituted imidazopyrimidines was synthetized and examined for its antifungal activity in several species.