2-Amino-4-methylpyrimidine supplier

Name
2-AMINO-4-METHYLPYRIMIDINE
EINECS 203-591-5
CAS No. 108-52-1
Article Data54
CAS DataBase
Density 1.155 g/cm³
Solubility
Melting Point 158-160 °C(lit.)
Formula C₅H₇N₃
Boiling Point 283.4 °C at 760 mmHg
Molecular Weight 109.131
Flash Point 149.9 °C
Transport Information
Appearance off-white to light brown crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 6-Methyl-2-pyrimidinamine;4-Methyl-2-aminopyrimidine;4-Methyl-2-pyrimidinamine;NSC 1939;Pyrimidine,2-amino-4-methyl- (6CI,7CI,8CI);2-Amino-6-methylpyrimidine;
PSA 51.80000
LogP 0.94840

Synthetic route

: 17321-93-6
5-bromo-4-methylpyrimidine-2-ylamine

: 73183-34-3
bis(pinacol)diborane

A: 108-52-1
4-Methyl-pyrimidin-2-ylamin

B: 944401-55-2
4-methyl-5-(4,4,5,5-tetramethyl (1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine

Conditions

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;

...Expand

: 5436-21-5
acetylacetaldehyde dimethyl acetal

: 50-01-1
guanidine hydrochloride

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 50-01-1
guanidine hydrochloride

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 5600-21-5
2-amino-6-methyl-4-chloropyrimidine

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 593-85-1
diguanidine carbonate

: 119490-02-7
3-(4-morpholinyl)-3-buten-2-one

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

guanidine salt of/the/ compound: guanidine salt of/the/ compound

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 81633-29-6
2-amino-4-methylpyrimidine-5-carboxylic acid ethyl ester

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 134653-70-6, 51145-57-4
ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 769-51-7
2-amino-4-methylpyrimidine-5-carboxylic acid

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

Conditions	Yield
for 2h; Heating;	83%

: 5424-21-5
2,4-dichloro-6-methylpyrimidine

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 3977-29-5
2-amino-6-methylpyrimidin-4-ol

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

: 64-17-5
ethanol

: 506-93-4
guanidine nitrate

sodium hydroxymethylenacetone: sodium hydroxymethylenacetone

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

Conditions	Yield
analoge Reaktionen mit anderen Hydroxymethylenketonen bzw.Dioxoverbindungen;

...Expand

: 67-56-1
methanol

: 5600-21-5
2-amino-6-methyl-4-chloropyrimidine

zinc: zinc

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

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

...Expand

: 113-00-8
guanidine nitrate

1.1.3-trichloro-butene-(2): 1.1.3-trichloro-butene-(2)

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

Conditions	Yield
und analoge Reaktionen;

: 4652-27-1
4-methoxy-3-buten-2-one

: 506-93-4
guanidine nitrate

sodium hydroxide: sodium hydroxide

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

...Expand

: 5600-21-5
2-amino-6-methyl-4-chloropyrimidine

: 7732-18-5
water

zinc dust: zinc dust

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

...Expand

: 64-17-5
ethanol

: 4652-27-1
4-methoxy-3-buten-2-one

: 141-52-6
sodium ethanolate

: 506-93-4
guanidine nitrate

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 773147-11-8
(2,2,5,7,8-pentamethylchroman-6-sulfonyl)isothiocyanate

: 947748-45-0
N-2,2,5,7,8-pentamethylchroman-6-sulfonyl-N'-2-(4-methylpyrimidyl)thiourea

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 105-36-2
ethyl bromoacetate

: 2-hydroxy-7-methylimidazo[1,2-a]pyrimidine

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 17321-93-6
5-bromo-4-methylpyrimidine-2-ylamine

Conditions

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%

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 4-(chlorosulfonyl)benzenesulfonyl fluoride

: 4-(N-(4-methylpyrimidin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 85-43-8
1,2,3,6-Tetrahydrophthalic anhydride

: 897392-57-3
N-(4-methylpyrimidin-2-yl)-1,2,3,6-tetrahydro-phthalimide

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 90-02-8
salicylaldehyde

: 105-56-6
ethyl 2-cyanoacetate

: C15H12N4O2

Conditions

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%

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 122-51-0
orthoformic acid triethyl ester

: 762-04-9
phosphonic acid diethyl ester

: tetraethyl [(4-methylpyrimidin-2-ylamino)methylene]bis(phosphonate)

Conditions

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

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 348640-06-2
4-bromo-7-azaindole

: 1248587-72-5
N-(4-methylpyrimidin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine

Conditions

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%

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 766-51-8
2-Chloroanisole

: 1445086-52-1
C12H13N3O

Conditions

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%

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 56952-04-6
methyl 2-N-benzoylamino-3-N,N-dimethylamino-2-propenoate

: methyl (Z)-2-benzoylamino-3-(4-methyl-2-pyrimidinyl)aminopropenoate

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 582-17-2
2,7-Dihydroxynaphthalene

: 90-02-8
salicylaldehyde

: 1393090-72-6
1-(2-hydroxyphenyl(2-(4-methylpyrimidinyl)amino)methyl)naphthalene-2,7-diol

Conditions

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

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 147116-69-6
N-(2,2-Dichloro-2-phenylethylidene)benzenesulfonamide

: N-{2,2-dichloro-1-[(4-methylpyrimidin-2-yl)amino]-2-phenylethyl}benzenesulfonamide

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 26035-31-4, 14913-33-8, 15663-27-1
transplatin

: Pt(NH3)2(NH2(C4H2N2)CH3)2(2+)*2Cl(1-) = {Pt(NH3)2(NH2(C4H2N2)CH3)2}Cl2

Conditions

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%

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 13089-11-7
methyl 3,3,3-trifluoropyruvate

: 1255787-69-9
methyl 2-[(4-methylpyrimidin-2-yl)imino]-3,3,3-trifluoropropanoate

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: C12H15NO4S

: 2-methyl-N-((4-methylpyrimidin-2-yl)carbamoyl)-5-vinylbenzenesulfonamide

Conditions

Conditions	Yield
In ethanol; toluene Reflux;	90%

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 61397-54-4
2-bromo-1-(2-chloro-4-fluorophenyl)ethan-1-one

: 2-(2-chloro-4-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 145100-50-1
1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)-sulfonyl)methanesulfonamide

: 2-N'-monotrifluoromethanesulfonamido-4-methylpyrimidine

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 582-17-2
2,7-Dihydroxynaphthalene

: 623-27-8
terephthalaldehyde,

: 1447758-42-0
1,4-bis[(4-methylpyrimidinyl-2-ylamino)(2,7-dihydroxynaphthalene-1-yl)methyl]benzene

Conditions

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

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 50-00-0
formaldehyd

: 123-08-0
4-hydroxy-benzaldehyde

: C14H13N3O2

Conditions

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%

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 90-15-3
α-naphthol

: 90-02-8
salicylaldehyde

: 1393090-68-0
2-(2-hydroxyphenyl(2-(4-methylpyrimidin-2-yl)amino)methyl)naphthalene-1-ol

Conditions

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

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 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

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%

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 403-29-2
2-bromo-4'-fluoroacetophenone

: 955-75-9
2-(4-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 90-02-8
salicylaldehyde

: 135-19-3
β-naphthol

: 1393090-65-7
1-(2-hydroxyphenyl(2-(4-methylpyrimidinyl)amino)methyl)naphthalene-2-ol

Conditions

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

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 68-11-1
mercaptoacetic acid

: 105-07-7
4-cyanobenzaldehyde

: 1610829-13-4
4-(3-(4-methylpyrimidin-2-yl)-4-oxothiazolidin-2-yl)benzonitrile

Conditions

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

...Expand

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 100-51-6
benzyl alcohol

: benzyl-(4-phenethylpyrimidin-2-yl)amine

Conditions

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%

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 199915-38-3
9-fluorenylmethoxycarbonyl isothiocyanate

: 1-Fmoc-3-(4-methylpyrimidin-2-yl)thiourea

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 15781-70-1
malonic acid bis-(2,4,6-trichloro-phenyl) ester

: 1227926-30-8
2-hydroxy-8-methyl-4H-pyrimido[1,2-a]pyrimidin-4-one

Conditions

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

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

: 105-13-5
4-Methoxybenzyl alcohol

: 1206484-75-4
(4-methoxybenzyl)-{4-[2-(4-methoxyphenyl)ethyl]pyrimidin-2-yl}amine

Conditions

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%

2-Amino-4-methylpyrimidine Specification

The 2-Pyrimidinamine,4-methyl- is an organic compound with the formula C₅H₇N₃. The IUPAC name of this chemical is 4-methylpyrimidin-2-amine. With the CAS registry number 108-52-1 and EINECS 203-591-5, it is also named as 6-Methyl-2-pyrimidinamine. The product's categoriesare Pyrimidine; Pyridines, Pyrimidines, Purines and Pteredines; Building Blocks; Heterocyclic Building Blocks. It is off-white to light brown crystalline powder which must be kept away from oxide. Additionally, this chemical should be stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.21; (4)ACD/LogD (pH 7.4): 0.24; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 30.17; (8)ACD/KOC (pH 7.4): 32.15; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.581; (13)Molar Refractivity: 31.49 cm³; (14)Molar Volume: 94.4 cm³; (15)Polarizability: 12.48×10^-24 cm³; (16)Surface Tension: 56.6 dyne/cm; (17)Enthalpy of Vaporization: 52.23 kJ/mol; (18)Vapour Pressure: 0.00317 mmHg at 25°C; (19)Tautomer Count: 6; (20)Exact Mass: 109.063997; (21)MonoIsotopic Mass: 109.063997; (22)Topological Polar Surface Area: 51.8; (23)Heavy Atom Count: 8; (24)Complexity: 74.1.

Uses of 2-Pyrimidinamine,4-methyl-: It can react with 2-benzoylamino-3-dimethylamino-acrylic acid methyl ester to get methyl (Z)-2-benzoylamino-3-(4-methyl-2-pyrimidinyl)aminopropenoate. This reaction needs solvents ethanol and aq. HCl. The reaction time is 3 hours. The yield is 92%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:n1c(ccnc1N)C
2. InChI:InChI=1/C5H7N3/c1-4-2-3-7-5(6)8-4/h2-3H,1H3,(H2,6,7,8)
3. InChIKey:GHCFWKFREBNSPC-UHFFFAOYAO

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	intravenous	730mg/kg (730mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950.

Product Name

2-AMINO-4-METHYLPYRIMIDINE

Synthetic route

2-Amino-4-methylpyrimidine Specification

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