108-52-1

Basic information

• Product Name: 2-AMINO-4-METHYLPYRIMIDINE
• Synonyms: TIMTEC-BB SBB004343;2-amino-4-methyl-pyrimidin;2-Pyrimidinamine, 4-methyl-;4-Methyl-2-pyrimidinamine;6-Methyl-2-pyrimidinamine;Pyrimidine, 2-amino-4-methyl-;2-AMINO-4-METHYLPYRIMIDINE;2-AMINO-4-METHYL-1,3-DIAZINE
• CAS NO: 108-52-1
• Molecular Formula: C₅H₇N₃
• Molecular Weight: 109.13
• EINECS: 203-591-5
• Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Building Blocks;Heterocyclic Building Blocks;Pyrimidines;Heterocycle-Pyrimidine series
• Mol File: 108-52-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 158-160 °C(lit.)
• Boiling Point: 194.6°C (rough estimate)
• Flash Point: 149.9 °C
• Appearance: Off-white to light brown/Crystalline Powder
• Density: 1 g/cm3
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: 1.5340 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: pK1: 4.11(+1) (20°C)
• BRN: 108506
• CAS DataBase Reference: 2-AMINO-4-METHYLPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-METHYLPYRIMIDINE(108-52-1)
• EPA Substance Registry System: 2-AMINO-4-METHYLPYRIMIDINE(108-52-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UV6485000
• Hazardous Substances Data: 108-52-1(Hazardous Substances Data)

Usage

Chemical Properties

OFF-WHITE TO LIGHT BROWN CRYSTALLINE POWDER

Uses

2-Amino-4-methylpyrimidine is a compound involved in a study about carbonylation as a key reaction in anaerobic acetone activation by Desulfococcus biacutus. 2-Amino-4-methylpyrimidine is formed as the product of a reaction between acetoacetaldehyde and guanidine.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 3526, 1951 DOI: 10.1021/ja01151a529

Purification Methods

Crystallise the pyrimidine from H2O or EtOH and sublime it in a vacuum. The picrate crystallises from EtOH and has m 235-236o(dec). [Beilstein 24 H 84, 25 III/IV 2152.]

InChI:InChI=1/C6H8N2/c1-5-3-2-4-8-6(5)7/h2-4H,1H3,(H2,7,8)

Synthetic route

5-bromo-4-methylpyrimidine-2-ylamine (17321-93-6) + bis(pinacol)diborane (73183-34-3) → 4-Methyl-pyrimidin-2-ylamin (108-52-1) + 4-methyl-5-(4,4,5,5-tetramethyl (1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine (944401-55-2)

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 115℃; for 18.25h; Heating / reflux;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 115℃; for 18h; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 115℃; for 16h; Suzuki Coupling; Inert atmosphere; Overall yield = 40 mg;

acetylacetaldehyde dimethyl acetal (5436-21-5) + guanidine hydrochloride (50-01-1) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
Stage #1: guanidine hydrochloride With sodium methylate In toluene at 28 - 35℃; for 2h; Stage #2: acetylacetaldehyde dimethyl acetal In toluene at 55 - 110℃; for 3h; Reagent/catalyst; Solvent;	77 g

4-trimethylsilyl-3-butyn-2-one (5930-98-3) + guanidine hydrochloride (50-01-1) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
With sodium carbonate In acetonitrile at 120℃; for 0.666667h; microwave irradiation;	90%

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
With water; zinc
bei der elektrochemischen Reduktion an einer Zink-Kathode;
With potassium hydroxide; palladium on activated charcoal Hydrogenation;

diguanidine carbonate (593-85-1) + 3-(4-morpholinyl)-3-buten-2-one (119490-02-7) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene

guanidine salt of/the/ compound → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
With but-1-en-3-ynyl-methyl ether; sulfuric acid
With ethyl-but-1-en-3-ynyl ether; sulfuric acid
With chromium(III) oxide; sulfuric acid; but-3-yn-2-ol

2-amino-4-methylpyrimidine-5-carboxylic acid ethyl ester (81633-29-6) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / KOH / methanol / 5 h / Heating 2: 83 percent / 2 h / Heating View Scheme

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6, 51145-57-4) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / NaOEt / ethanol / 1 h / Heating 2: 93 percent / KOH / methanol / 5 h / Heating 3: 83 percent / 2 h / Heating View Scheme

2-amino-4-methylpyrimidine-5-carboxylic acid (769-51-7) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
for 2h; Heating;	83%

2,4-dichloro-6-methylpyrimidine (5424-21-5) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH3 2: palladium/SrCO3; aqueous KOH; acetone / Hydrogenation View Scheme
Multi-step reaction with 2 steps 1: alcohol; ammonia / im Rohr 2: zinc dust; water View Scheme

2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus oxychloride / Heating 2: zinc dust; aq. ammonium chloride / Heating View Scheme

ethanol (64-17-5) + guanidine nitrate (506-93-4) + sodium hydroxymethylenacetone → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
analoge Reaktionen mit anderen Hydroxymethylenketonen bzw.Dioxoverbindungen;

methanol (67-56-1) + 2-amino-6-methyl-4-chloropyrimidine (5600-21-5) + zinc → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
at 60 - 65℃; Elektrolytische Reduktion vom pH 7.9;

guanidine nitrate (113-00-8) + 1.1.3-trichloro-butene-(2) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

Conditions	Yield
und analoge Reaktionen;

4-methoxy-3-buten-2-one (4652-27-1) + guanidine nitrate (506-93-4) + sodium hydroxide → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) + water (7732-18-5) + zinc dust → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

ethanol (64-17-5) + 4-methoxy-3-buten-2-one (4652-27-1) + sodium ethanolate (141-52-6) + guanidine nitrate (506-93-4) → 4-Methyl-pyrimidin-2-ylamin (108-52-1)

4-Methyl-pyrimidin-2-ylamin (108-52-1) + (2,2,5,7,8-pentamethylchroman-6-sulfonyl)isothiocyanate (773147-11-8) → N-2,2,5,7,8-pentamethylchroman-6-sulfonyl-N'-2-(4-methylpyrimidyl)thiourea (947748-45-0)

Conditions	Yield
In dichloromethane at 20℃; for 24h;	100%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + ethyl bromoacetate (105-36-2) → 2-hydroxy-7-methylimidazo[1,2-a]pyrimidine

Conditions	Yield
With ethanol for 4h; Concentration; Reflux;	100%

4-Methyl-pyrimidin-2-ylamin (108-52-1) → 5-bromo-4-methylpyrimidine-2-ylamine (17321-93-6)

Conditions	Yield
Stage #1: 4-Methyl-pyrimidin-2-ylamin With N-Bromosuccinimide In chloroform for 15h; Stage #2: With sodium hydroxide In dichloromethane; chloroform; water	99%
With N-Bromosuccinimide In chloroform for 15h; Darkness;	99%
With N-Bromosuccinimide In chloroform at 20℃; for 2h;	91%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 4-(chlorosulfonyl)benzenesulfonyl fluoride → 4-(N-(4-methylpyrimidin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

Conditions	Yield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;	99%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 1,2,3,6-Tetrahydrophthalic anhydride (85-43-8) → N-(4-methylpyrimidin-2-yl)-1,2,3,6-tetrahydro-phthalimide (897392-57-3)

Conditions	Yield
With dicyclohexyl-carbodiimide In toluene Reflux;	98%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + salicylaldehyde (90-02-8) + ethyl 2-cyanoacetate (105-56-6) → C15H12N4O2

Conditions	Yield
With (N-propyl)-1,3,5,7-tetraazaadamantan-1-ium chloride functionalized silica-coated calcium oxide nano hybrid In neat (no solvent) at 80℃; for 0.25h;	95%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + orthoformic acid triethyl ester (122-51-0) + phosphonic acid diethyl ester (762-04-9) → tetraethyl [(4-methylpyrimidin-2-ylamino)methylene]bis(phosphonate)

Conditions	Yield
With copper(II) oxide In neat (no solvent) at 60℃; Microwave irradiation; Green chemistry;	94%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 4-bromo-7-azaindole (348640-06-2) → N-(4-methylpyrimidin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine (1248587-72-5)

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	93%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 2-Chloroanisole (766-51-8) → C12H13N3O (1445086-52-1)

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; C47H63NO2PPd(2+)*CH3O3S(1-); sodium t-butanolate In tert-butyl alcohol at 100℃; for 8h;	93%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; sodium t-butanolate In tert-butyl alcohol at 100℃; for 8h; Inert atmosphere;	93%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + methyl 2-N-benzoylamino-3-N,N-dimethylamino-2-propenoate (56952-04-6) → methyl (Z)-2-benzoylamino-3-(4-methyl-2-pyrimidinyl)aminopropenoate

Conditions	Yield
In hydrogenchloride; ethanol for 3h; Heating;	92%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 2,7-Dihydroxynaphthalene (582-17-2) + salicylaldehyde (90-02-8) → 1-(2-hydroxyphenyl(2-(4-methylpyrimidinyl)amino)methyl)naphthalene-2,7-diol (1393090-72-6)

Conditions	Yield
at 80℃; for 0.5h; Mannich type reaction; neat (no solvent);	91%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + N-(2,2-Dichloro-2-phenylethylidene)benzenesulfonamide (147116-69-6) → N-{2,2-dichloro-1-[(4-methylpyrimidin-2-yl)amino]-2-phenylethyl}benzenesulfonamide

Conditions	Yield
In 1,4-dioxane at 20℃; for 6h;	91%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + transplatin (26035-31-4, 14913-33-8, 15663-27-1) → Pt(NH3)2(NH2(C4H2N2)CH3)2(2+)*2Cl(1-) = {Pt(NH3)2(NH2(C4H2N2)CH3)2}Cl2

Conditions	Yield
In water heated in boiling water bath for 1 h; evapd., cooled, acetone added, filtered, washed (acetone), dried at 70-80°C, elem. anal.;	90%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + methyl 3,3,3-trifluoropyruvate (13089-11-7) → methyl 2-[(4-methylpyrimidin-2-yl)imino]-3,3,3-trifluoropropanoate (1255787-69-9)

Conditions	Yield
Stage #1: 4-Methyl-pyrimidin-2-ylamin; methyl 3,3,3-trifluoropyruvate In benzene at 20℃; for 1h; Stage #2: With thionyl chloride In benzene at 20℃; for 0.25h; Stage #3: With pyridine In benzene at 0 - 20℃;	90%
Stage #1: 4-Methyl-pyrimidin-2-ylamin; methyl 3,3,3-trifluoropyruvate With thionyl chloride In benzene at 5 - 20℃; Stage #2: With pyridine

4-Methyl-pyrimidin-2-ylamin (108-52-1) + C12H15NO4S → 2-methyl-N-((4-methylpyrimidin-2-yl)carbamoyl)-5-vinylbenzenesulfonamide

Conditions	Yield
In ethanol; toluene Reflux;	90%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 2-bromo-1-(2-chloro-4-fluorophenyl)ethan-1-one (61397-54-4) → 2-(2-chloro-4-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

Conditions	Yield
In ethanol for 5h; Reflux;	90%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)-sulfonyl)methanesulfonamide (145100-50-1) → 2-N'-monotrifluoromethanesulfonamido-4-methylpyrimidine

Conditions	Yield
In acetonitrile at 60℃; Inert atmosphere;	90%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 2,7-Dihydroxynaphthalene (582-17-2) + terephthalaldehyde, (623-27-8) → 1,4-bis[(4-methylpyrimidinyl-2-ylamino)(2,7-dihydroxynaphthalene-1-yl)methyl]benzene (1447758-42-0)

Conditions	Yield
With formic acid In neat (no solvent) at 80℃; for 0.333333h; Mannich Aminomethylation; Green chemistry;	89%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + formaldehyd (50-00-0) + 4-hydroxy-benzaldehyde (123-08-0) → C14H13N3O2

Conditions	Yield
Stage #1: 4-Methyl-pyrimidin-2-ylamin; formaldehyd In 1,4-dioxane for 0.8h; Stage #2: 4-hydroxy-benzaldehyde In 1,4-dioxane at 70℃; for 6h;	89%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + α-naphthol (90-15-3) + salicylaldehyde (90-02-8) → 2-(2-hydroxyphenyl(2-(4-methylpyrimidin-2-yl)amino)methyl)naphthalene-1-ol (1393090-68-0)

Conditions	Yield
at 80℃; for 0.416667h; Mannich type reaction; neat (no solvent);	88%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + tert-butyl 4-(10-bromo-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate → tert-butyl 4-{10-[(4-methylpyrimidin-2-yl)amino]-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl}piperidine-1-carboxylate

Conditions	Yield
With potassium phosphate; t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In tert-butyl alcohol at 95℃; for 16h; Inert atmosphere;	88%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 2-bromo-4'-fluoroacetophenone (403-29-2) → 2-(4-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine (955-75-9)

Conditions	Yield
In ethanol for 5h; Reflux;	88%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + salicylaldehyde (90-02-8) + β-naphthol (135-19-3) → 1-(2-hydroxyphenyl(2-(4-methylpyrimidinyl)amino)methyl)naphthalene-2-ol (1393090-65-7)

Conditions	Yield
at 80℃; for 0.5h; Mannich type reaction; neat (no solvent);	87%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + mercaptoacetic acid (68-11-1) + 4-cyanobenzaldehyde (105-07-7) → 4-(3-(4-methylpyrimidin-2-yl)-4-oxothiazolidin-2-yl)benzonitrile (1610829-13-4)

Conditions	Yield
In toluene Reflux; Dean-Stark;	86.8%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + benzyl alcohol (100-51-6) → benzyl-(4-phenethylpyrimidin-2-yl)amine

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Py2NPiPr2; potassium tert-butylate In tetrahydrofuran; diethylene glycol dimethyl ether at 110℃; for 24h; Inert atmosphere;	85%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 9-fluorenylmethoxycarbonyl isothiocyanate (199915-38-3) → 1-Fmoc-3-(4-methylpyrimidin-2-yl)thiourea

Conditions	Yield
In 1,4-dioxane Inert atmosphere; Reflux;	85%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + malonic acid bis-(2,4,6-trichloro-phenyl) ester (15781-70-1) → 2-hydroxy-8-methyl-4H-pyrimido[1,2-a]pyrimidin-4-one (1227926-30-8)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 6h; regioselective reaction;	84%

4-Methyl-pyrimidin-2-ylamin (108-52-1) + 4-Methoxybenzyl alcohol (105-13-5) → (4-methoxybenzyl)-{4-[2-(4-methoxyphenyl)ethyl]pyrimidin-2-yl}amine (1206484-75-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Py2NPiPr2; potassium tert-butylate In tetrahydrofuran; diethylene glycol dimethyl ether at 110℃; for 24h; Inert atmosphere;	83%

Upstream product

• 4652-27-1 4-methoxy-3-buten-2-one 
• 506-93-4 guanidine nitrate 
• 17321-93-6 5-bromo-4-methylpyrimidine-2-ylamine 
• 73183-34-3 bis(pinacol)diborane 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 50-01-1 guanidine hydrochloride 
• 593-85-1 diguanidine carbonate 
• 119490-02-7 3-(4-morpholinyl)-3-buten-2-one 
• 5424-21-5 2,4-dichloro-6-methylpyrimidine 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 81633-29-6 2-amino-4-methylpyrimidine-5-carboxylic acid ethyl ester 
• 3977-29-5 2-amino-6-methylpyrimidin-4-ol 
• 5930-98-3 4-trimethylsilyl-3-butyn-2-one 
• 64-17-5 ethanol 

Downstream Products

• 124211-79-6 N,N-Dimethyl-N'-(4-methyl-pyrimidin-2-yl)-formamidine 
• 1104066-51-4 2-(2,6-dibromophenyl)-3-(4-methylpyrimidin-2-yl)thiazolidin-4-one 
• 1206484-76-5 (3-methylbenzyl)-[4-(2-m-tolylethyl)pyrimidin-2-yl]amine 
• 1206484-75-4 (4-methoxybenzyl)-{4-[2-(4-methoxyphenyl)ethyl]pyrimidin-2-yl}amine 
• 25710-14-9 N-benzyl-(4-methylpyrimidin-2-yl)amine 
• 50324-58-8 4-phenethyl-pyrimidin-2-ylamine 
• 1227926-40-0 3-(cyclohex-2-en-1-yl)-2-hydroxy-8-methyl-4H-pyrimido[1,2-a]pyrimidin-4-one 
• 1227926-30-8 2-hydroxy-8-methyl-4H-pyrimido[1,2-a]pyrimidin-4-one 
• 1393090-68-0 2-(2-hydroxyphenyl(2-(4-methylpyrimidin-2-yl)amino)methyl)naphthalene-1-ol 
• 1393090-72-6 1-(2-hydroxyphenyl(2-(4-methylpyrimidinyl)amino)methyl)naphthalene-2,7-diol 

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A new Cd(II) complex with the monodentate ligand 2-amino-4-methylpyrimidine, [Cd(NO3)2(C5N3H7)2(H2O)2], has been prepared and characterized by single crystal X-ray diffraction, elemental analysis, CP–MAS NMR and IR spectroscopy. The basic coordination patterns of the 2-amino-4-methylpyrimidine ...detailed

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