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

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

Uses

Used in Pharmaceutical Research:
2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride is used as a research tool for studying the role of serotonin receptors, specifically the 5-HT1A receptor, in various physiological and pathological processes. Its antagonistic action on the 5-HT1A receptor aids in understanding the mechanisms of serotonin signaling and its implications in mental health disorders.
Used in Drug Development:
In the development of pharmaceuticals, 2-(4-(piperazin-1-yl)phenyl)pyrimidine hydrochloride serves as a lead compound for the creation of new medications targeting the 5-HT1A receptor. Its potential therapeutic applications are being explored for the treatment of conditions such as anxiety, depression, and schizophrenia, where modulation of serotonin signaling is believed to be beneficial.
Used in Biological and Pharmacological Research Settings:
The hydrochloride salt form of 2-(4-(piperazin-1-yl)phenyl)pyrimidine is used to improve the compound's solubility and stability, facilitating its use in various experimental setups and assays within biological and pharmacological research. This enhanced stability allows for more reliable and reproducible results in studies investigating the compound's interactions with the 5-HT1A receptor and its effects on related physiological processes.

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

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

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.

POLYCYCLIC INDAZOLE DERIVATIVES THAT ARE 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.

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).