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
• Article Data: 3

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

• 64-17-5 ethanol 
• 3699-10-3 2-ethoxymethyl-3c-methoxy-acrylonitrile 
• 124-42-5 acetamidine hydrochloride 
• 141-52-6 sodium ethanolate 
• 763-69-9 ethyl 3-ethoxypropionate 
• 5423-97-2 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one 
• 109-95-5 ethyl nitrite 
• 874-43-1 5-(aminomethyl)-2-methylpyrimidin-4-amine dihydrochloride 
• 749835-80-1 2-methyl-5-ethoxymethyl-6-chloropyrimidine 
• 2141-62-0 3-(ethoxy)propionitrile 
• 99764-73-5 3-t-butoxypropanenitrile 
• 109-94-4 formic acid ethyl ester 
• 143-37-3 acetamidine 
• 71-43-2 benzene 

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

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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.