73-66-5

Basic information

• Product Name: 5-ethoxymethyl-2-methylpyrimidin-4-ylamine
• Synonyms: 5-ethoxymethyl-2-methylpyrimidin-4-ylamine;2-Methyl-5-(ethoxymethyl)pyrimidine-4-amine;5-(Ethoxymethyl)-2-methyl-4-pyrimidinamine;4-AMino-5-ethoxyMethyl-2-MethylpyriMidine;2-Methyl-4-amino-5-ethoxymethylpyrimidine;MFCD00223754;Pyrimidine, 4-amino-5-(ethoxymethyl)-2-methyl-
• CAS NO: 73-66-5
• Molecular Formula: C₈H₁₃N₃O
• Molecular Weight: 167.20832
• EINECS: 200-802-2
• Mol File: 73-66-5.mol

Chemical Properties

• Boiling Point: 295.79°C (rough estimate)
• Flash Point: 121°C
• Appearance: /
• Density: 1.1283 (rough estimate)
• Vapor Pressure: 0.0048mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 5-ethoxymethyl-2-methylpyrimidin-4-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ethoxymethyl-2-methylpyrimidin-4-ylamine(73-66-5)
• EPA Substance Registry System: 5-ethoxymethyl-2-methylpyrimidin-4-ylamine(73-66-5)

Safety Data

• Hazardous Substances Data: 73-66-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-white Solid

InChI:InChI=1/C8H13N3O/c1-3-12-5-7-4-10-6(2)11-8(7)9/h4H,3,5H2,1-2H3,(H2,9,10,11)

Synthetic route

2-methyl-5-ethoxymethyl-6-chloropyrimidine (749835-80-1) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
With ammonia In methanol at 140℃; for 4.5h; Autoclave;	82%
With ethanol; ammonia at 140℃;

ethyl nitrite (109-95-5) + 5-(aminomethyl)-2-methylpyrimidin-4-amine dihydrochloride (874-43-1, 1195-07-9, 25449-06-3) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
With ethanol at 90 - 100℃;

ethanol (64-17-5) + 2-ethoxymethyl-3c-methoxy-acrylonitrile (3699-10-3) + acetamidine hydrochloride (124-42-5) + sodium ethanolate (141-52-6) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

2-ethoxymethyl-3c-methoxy-acrylonitrile (3699-10-3) + acetamidine (143-37-3) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
With ethanol

3c-ethoxy-2-ethoxymethyl-acrylonitrile (3699-12-5) + acetamidine (143-37-3) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
With ethanol

3-acetoxy-2-ethoxymethyl-acrylonitrile + acetamidine (143-37-3) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
With ethanol; benzene

ethanol (64-17-5) + 3-acetoxy-2-ethoxymethyl-acrylonitrile + acetamidine (143-37-3) + benzene (71-43-2) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
Erwaermen des Reaktionsprodukts mit 10prozentig.KOH;
Erwaermen des Reaktionsprodukts mit 10prozentig.KOH;Geschwindigkeit;

3-t-butoxypropanenitrile (99764-73-5) + acetamidine hydrochloride (124-42-5) + formic acid ethyl ester (109-94-4) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) + 2-methyl-4-amino-5-tert-butoxymethylpyrimidine (127556-60-9)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

3-(ethoxy)propionitrile (2141-62-0) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl formate; benzene / beim Erwaermen des Reaktionsgemisches mit Dimethylsulfat 2: ethanol View Scheme
Multi-step reaction with 2 steps 1: ethyl formate; benzene / beim Erwaermen des Reaktionsgemisches mit Diaethylsulfat 2: ethanol 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

ethyl 3-ethoxypropionate (763-69-9) → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium / diethyl ether / 8 h / 20 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: triethylamine; trichlorophosphate / 3 h / 78 °C 3.1: ammonia / methanol / 4.5 h / 140 °C / Autoclave View Scheme

2-methyl-5-ethoxymethyl-6-hydroxypyrimidine → 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; trichlorophosphate / 3 h / 78 °C 2: ammonia / methanol / 4.5 h / 140 °C / Autoclave View Scheme

5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) → 4-amino-5-bromomethyl-2-methylpyrimidine hydrobromide (2908-71-6)

Conditions	Yield
With hydrogen bromide; acetic acid at 20 - 100℃; for 2h;	81%

5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) → 5-bromomethyl-2-methyl-pyrimidin-4-ylamine (25526-81-2)

Conditions	Yield
With hydrogen bromide; acetic acid

5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) → 5-(chloromethyl)-2-methyl-pyrimidin-4-amine (189745-28-6)

Conditions	Yield
With hydrogenchloride; butan-1-ol

5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) → 4-Amino-5-chloromethyl-2-methylpyrimidinium hydrochloride (70476-08-3) + 2-methyl-4-chloro-5-chloromethylpyrimidine hydrochloride + 2-methyl-4-chloro-5-hydroxymethylpyrimidine hydrochloride + 2-methyl-4-chloro-5-ethoxymethylpyrimidine hydrochloride

Conditions	Yield
With hydrogenchloride at 90 - 95℃; for 5h; Substitution; Title compound not separated from byproducts;

5-hydroxyethyl-4-methylthiazole (137-00-8) + 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) → Thiamine hydrochloride (67-03-8)

Conditions	Yield
Stage #1: 5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine With hydrogenchloride In water at 90 - 95℃; for 5h; Substitution; Stage #2: 5-hydroxyethyl-4-methylthiazole at 102℃; for 4h; Alkylation;	0.85 g

5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) → Aneurin (70-16-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; HBr View Scheme

5-ethoxymethyl-2-methyl-pyrimidin-4-ylamine (73-66-5) → 18F-deoxythiamine

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; hydrogen bromide / 2 h / 20 - 100 °C 2: acetonitrile / 0.33 h / 110 °C View Scheme

Upstream product

• 749835-80-1 2-methyl-5-ethoxymethyl-6-chloropyrimidine 
• 109-95-5 ethyl nitrite 
• 874-43-1 5-(aminomethyl)-2-methylpyrimidin-4-amine dihydrochloride 
• 64-17-5 ethanol 
• 3699-10-3 2-ethoxymethyl-3c-methoxy-acrylonitrile 
• 124-42-5 acetamidine hydrochloride 
• 141-52-6 sodium ethanolate 
• 143-37-3 acetamidine 
• 3699-12-5 3c-ethoxy-2-ethoxymethyl-acrylonitrile 
• 71-43-2 benzene 
• 99764-73-5 3-t-butoxypropanenitrile 
• 109-94-4 formic acid ethyl ester 
• 2141-62-0 3-(ethoxy)propionitrile 
• 763-69-9 ethyl 3-ethoxypropionate 

Downstream Products

• 25526-81-2 5-bromomethyl-2-methyl-pyrimidin-4-ylamine 
• 189745-28-6 5-(chloromethyl)-2-methyl-pyrimidin-4-amine 
• 70476-08-3 4-Amino-5-chloromethyl-2-methylpyrimidinium hydrochloride 
• 67-03-8 Thiamine hydrochloride 
• 2908-71-6 4-amino-5-bromomethyl-2-methylpyrimidine hydrobromide 

Relevant articles and documents

RADIOISOTOPE 18F SUBSTITUTED THIAMINE, AND SYNTHESIS METHOD AND USE THEREOF

The present invention discloses a radioisotope 18F substituted thiamine, synthesis method, and use thereof in small animal PET/CT imaging. The radioisotope 18F substituted thiamine has a structure of The synthesis method comprises radiochemical synthesis by using existing precursors. In the present invention, the hydroxyl in the hydroxyethyl on the thiazole cycle of thiamine is replaced by radioisotope 18F, to prepare a PET tracer. The radioisotope 18F substituted thiamine of the present invention successfully enters the brains of various strains of mice, and the uptake in the brains of thiamine-deficient mice is obviously greater than that in normal control. The present invention is useful in the preparation of a brain imaging tracer for clinical trials of Alzheimer's disease and tumors.

Pyrimidine derivatives exhibiting antitumor activity

A compound represented by the formula (I): wherein, for example, R1, R2, R3, and R4 are each independently hydrogen atom, alky, and the like, R5 and R6 are each independently hydrogen atom, alkyl, and the like, X is —O—, —S—, and the like, Y is 5-membered heteroaryl-diyl and the like, Z is optionally substituted aryl and the like, the prodrugs thereof, or their pharmaceutically acceptable salts, or their solvates.