5423-97-2

Basic information

• Product Name: NSC 51127
• Synonyms: 5-(EthoxyMethyl)-2-Methyl-4(3H)-pyriMidinone, NSC 13143;5-(EthoxyMethyl)-2-Methyl-4-pyriMidinone;NSC 51126;NSC 51127
• CAS NO: 5423-97-2
• Molecular Formula: C₈H₁₂N₂O₂
• Molecular Weight: 168.19308
• Product Categories: Amines;Heterocycles;Protein Kinase Inhibitors and Activators
• Mol File: 5423-97-2.mol
• Article Data: 0

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.16g/cm³
• Refractive Index: 1.692
• Solubility: Chloroform, Dichloromethane, Methanol
• CAS DataBase Reference: NSC 51127(CAS DataBase Reference)
• NIST Chemistry Reference: NSC 51127(5423-97-2)
• EPA Substance Registry System: NSC 51127(5423-97-2)

Safety Data

• Hazardous Substances Data: 5423-97-2(Hazardous Substances Data)

Usage

Description

NSC 51127, also known as 5-(Ethoxymethyl)-2-methyl-4-pyrimidinone, is a white solid compound with demonstrated effects on increasing locomotor activity in mice. It serves as an intermediate in the preparation of G protein-coupled receptor kinase (GRK) inhibitors, which are important for various biological processes and potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
NSC 51127 is used as an intermediate for the synthesis of G protein-coupled receptor kinase (GRK) inhibitors. These inhibitors play a crucial role in regulating signal transduction pathways and have potential applications in treating various diseases and conditions related to the dysregulation of these pathways.
Used in Research and Development:
NSC 51127 is used as a research compound to study the effects of GRK inhibition on cellular processes and to develop new therapeutic strategies for diseases involving GRK dysregulation. Its ability to increase locomotor activity in mice also makes it a valuable tool for studying the underlying mechanisms of movement and behavior in preclinical research settings.
Used in Drug Discovery:
NSC 51127 is used as a starting point for the development of new drugs targeting GRKs. Its chemical properties and structure can be modified to create more potent and selective inhibitors, potentially leading to the discovery of novel therapeutic agents for a range of diseases.

InChI:InChI=1/C9H10N6OS2/c1-5-2-3-11-8(12-5)13-6(16)4-17-9-15-14-7(10)18-9/h2-3H,4H2,1H3,(H2,10,14)(H,11,12,13,16)

Synthetic route

5-bromomethyl-4,6-dichloro-2-methyl-pyrimidine (1780-34-3) + sodium ethanolate (141-52-6) → 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2)

Conditions	Yield
With ethanol anschliessenden Hydrieren an Palladium/Kohle und Behandeln mit konz.HCl;

4-bromo-5-bromomethyl-6-chloro-2-methyl-pyrimidine (856975-67-2) + sodium ethanolate (141-52-6) → 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2)

Conditions	Yield
With ethanol anschliessenden Hydrieren an Palladium/Kohle und Behandeln mit konz.HCl;

methyl acetimidate (14777-29-8, 85273-25-2) + β,β'-diethoxy-β-methoxy-isobutyric acid ethyl ester (91243-92-4) → 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2)

Conditions	Yield
With ammonia

β,β'-diethoxy-β-methoxy-isobutyric acid ethyl ester (91243-92-4) + acetamidine (143-37-3) → 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2)

acetamidine hydrochloride (124-42-5) + 2-ethoxymethyl-3ξ-methoxy-acrylic acid ethyl ester → 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2)

acetamidine hydrochloride (124-42-5) + sodium-compound of β-ethoxy-β'-oxo-isobutyric acid ethyl ester → 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2)

4,6-dichloro-2,5-dimethyl-pyrimidine (1780-33-2) → 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dibenzoyl peroxide; CCl4; N-bromo-succinimide 2: ethanol / anschliessenden Hydrieren an Palladium/Kohle und Behandeln mit konz.HCl View Scheme

5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2) → 2-methyl-5-ethoxymethyl-6-chloropyrimidine (749835-80-1)

Conditions	Yield
With trichlorophosphate

5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2) → (2-methyl-6-oxo-1,6-dihydro-pyrimidin-5-yl)-methanesulfonic acid (98135-20-7)

Conditions	Yield
With sulfur dioxide; water; sodium sulfite

5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2) → 5-bromomethyl-2-methyl-pyrimidin-4-ylamine (25526-81-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl3 2: ethanol; NH3 / 140 °C 3: acetic acid; HBr View Scheme

5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3 2: ethanol; NH3 / 140 °C View Scheme

5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one (5423-97-2) → Aneurin (70-16-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: POCl3 2: ethanol; NH3 / 140 °C 3: acetic acid; HBr View Scheme

Upstream product

• 14777-29-8 methyl acetimidate 
• 91243-92-4 β,β'-diethoxy-β-methoxy-isobutyric acid ethyl ester 
• 143-37-3 acetamidine 
• 1780-33-2 4,6-dichloro-2,5-dimethyl-pyrimidine 
• 124-42-5 acetamidine hydrochloride 
• 856975-67-2 4-bromo-5-bromomethyl-6-chloro-2-methyl-pyrimidine 
• 141-52-6 sodium ethanolate 
• 1780-34-3 5-bromomethyl-4,6-dichloro-2-methyl-pyrimidine 

Downstream Products

• 73-66-5 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine 
• 25526-81-2 5-bromomethyl-2-methyl-pyrimidin-4-ylamine