1056624-11-3

Basic information

• Product Name: 2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride
• Synonyms: 2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride;PyriMidine, 2-[4-(1-piperazinyl)phenyl]-, (Hydrochloride) (1:1);2-(4-Piperazin-1-yl-phenyl)-pyriMidine;2-(4-(PIPERAZIN-1-YL)PHENYL)PYRIMIDINE HCL
• CAS NO: 1056624-11-3
• Molecular Formula: C₁₄H₁₆N₄*ClH
• Molecular Weight: 276.76458
• Product Categories: intermediates
• Mol File: 1056624-11-3.mol
• Article Data: 3

Chemical Properties

• Appearance: Yellow power
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride(1056624-11-3)
• EPA Substance Registry System: 2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride(1056624-11-3)

Safety Data

• Hazardous Substances Data: 1056624-11-3(Hazardous Substances Data)

Usage

General Description

2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride is a chemical compound with the molecular formula C14H17N5?HCl. It is a pyrimidine derivative that contains a piperazine moiety and is used as a research tool in the study of serotonin receptors. The compound acts as a selective antagonist for the 5-HT1A receptor, which is a subtype of the serotonin receptor. This makes it a valuable tool for studying the role of serotonin signaling in various physiological and pathological processes. Additionally, it may have potential therapeutic applications in the treatment of conditions such as anxiety, depression, and schizophrenia. The hydrochloride salt form of the compound is commonly used for greater solubility and stability in biological and pharmacological research settings.

Synthetic route

4-(4-pyrimidin-2-yl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (942189-35-7) → 2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dichloromethane
With hydrogenchloride In 1,4-dioxane; dichloromethane for 2h;
With hydrogenchloride In 1,4-dioxane; dichloromethane for 2h;

C21H35BN2O4 → 2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonium chloride / tetrahydrofuran; hexanes; water / 0.08 h 1.2: 1 h 2.1: potassium carbonate / bis-triphenylphosphine-palladium(II) chloride / water; N,N-dimethyl-formamide / 8 h / 80 °C 3.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h View Scheme

tert-butyl 4-(4-bromophenyl)piperazine-1-carboxylate (352437-09-3) → 2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C 1.2: 18.17 h / 20 °C 2.1: ammonium chloride / tetrahydrofuran; hexanes; water / 0.08 h 2.2: 1 h 3.1: potassium carbonate / bis-triphenylphosphine-palladium(II) chloride / water; N,N-dimethyl-formamide / 8 h / 80 °C 4.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h View Scheme

4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenylboronic acid (457613-78-4) → 2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / bis-triphenylphosphine-palladium(II) chloride / water; N,N-dimethyl-formamide / 8 h / 80 °C 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h View Scheme

1-(4-Bromophenyl)Piperazine Monohydrochloride → 2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 1 h 2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C 2.2: 18.17 h / 20 °C 3.1: ammonium chloride / tetrahydrofuran; hexanes; water / 0.08 h 3.2: 1 h 4.1: potassium carbonate / bis-triphenylphosphine-palladium(II) chloride / water; N,N-dimethyl-formamide / 8 h / 80 °C 5.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h View Scheme

1-carboxymethyl-pyrrolidine-3-carboxylic acid methyl ester (942189-34-6) + 2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3) → 1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester (942189-36-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 24h;

1-tert-butoxycarbonylmethyl-3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester (1056623-86-9) + 2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3) → 3-methoxymethyl-1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester (942189-79-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In 1,2-dimethoxyethane for 4h;

2-(4-piperazin-1-yl-phenyl)-pyrimidine hydrochloride (1056624-11-3) + chloroacetyl chloride (79-04-9) → 2-chloro-1-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h;

Upstream product

• 457613-78-4 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenylboronic acid 
• 352437-09-3 tert-butyl 4-(4-bromophenyl)piperazine-1-carboxylate 
• 942189-35-7 4-(4-pyrimidin-2-yl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 942189-36-8 1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester 
• 942189-79-9 3-methoxymethyl-1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS AND USE THEREOF AS ERK INHIBITORS

Disclosed are the ERK inhibitors of formula 1.0: [Formula (1.0)] and the pharmaceutically acceptable salts, esters and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

PYRROLIDINE DERIVATIVES AS ERK INHIBITORS

Disclosed are the ERK inhibitors of Formula (1.0): and the pharmaceutically acceptable salts and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of Formula (1.0).