5-Pyrimidinecarbonitrile,4-amino-2-methyl- supplier

Name
4-AMINO-2-METHYLPYRIMIDINE-5-CARBONITRILE
EINECS 211-814-2
CAS No. 698-29-3
Article Data49
CAS DataBase
Density 1.27 g/cm³
Solubility Slightly soluble in water (6.4 g/L at 25°C). Soluble in dimethyl sulfoxide, ethanol and methanol.
Melting Point 249 °C
Formula C₆H₆N₄
Boiling Point 315.6 °C at 760 mmHg
Molecular Weight 134.14
Flash Point 144.7 °C
Transport Information
Appearance Pale-Yellow Crystalline Solid
Safety 26-39
Risk Codes Xn:Harmful;
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Methyl-4-amino-5-cyanopyrimidine;4-Amino-5-cyano-2-methylpyrimidine;5-Cyano-4-amino-2-methylpyrimidine;NSC459;Pynitrile;4-Amino-2-methylpyrimidine-5-carbonitrile;
PSA 75.59000
LogP 0.82008

Synthetic route

: 1445-45-0
Trimethyl orthoacetate

: 151-18-8
2-cyanoethylamine

: 420-04-2
CYANAMID

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: Trimethyl orthoacetate; 2-cyanoethylamine In methanol at 50 - 55℃; for 2h; Stage #2: CYANAMID In methanol at 55 - 60℃; for 3h; Temperature; Solvent; Further stages;	98.1%

...Expand

: ethanimidamide hydrochloride

: 16849-88-0
1-(dimethylamine)-2,2-dicyanoethylene

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: ethanimidamide hydrochloride With sodium methylate In methanol for 0.166667h; Cooling with ice; Stage #2: 1-(dimethylamine)-2,2-dicyanoethylene In methanol at 20℃; for 12.5h;	97%

: 151-18-8
2-cyanoethylamine

: 420-04-2
CYANAMID

: 72858-79-8
triisopropyl orthoacetate

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: 2-cyanoethylamine; triisopropyl orthoacetate In isopropyl alcohol at 50 - 55℃; for 2h; Stage #2: CYANAMID In isopropyl alcohol at 55 - 60℃; for 3h; Further stages;	93.3%

...Expand

: 50-00-0
formaldehyd

: 124-42-5
acetamidine hydrochloride

: 109-77-3
malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: formaldehyd; acetamidine hydrochloride; malononitrile In water; tert-butyl alcohol at 65 - 70℃; for 4h; Mannich Aminomethylation; Stage #2: With tert.-butylhydroperoxide In water; tert-butyl alcohol at 20 - 35℃; for 1h; Temperature; Solvent; Reagent/catalyst;	92.6%

...Expand

: 151-18-8
2-cyanoethylamine

: 420-04-2
CYANAMID

: 78-39-7
Triethyl orthoacetate

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: 2-cyanoethylamine; Triethyl orthoacetate In ethanol at 50 - 55℃; for 2h; Stage #2: CYANAMID In ethanol at 55 - 60℃; for 3h; Further stages;	91.8%

...Expand

: 16849-88-0
1-(dimethylamine)-2,2-dicyanoethylene

: 124-42-5
acetamidine hydrochloride

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: acetamidine hydrochloride With sodium methylate In methanol for 0.166667h; Cooling with ice; Large scale reaction; Stage #2: 1-(dimethylamine)-2,2-dicyanoethylene In methanol at 20℃; for 12.5h; Cooling; Large scale reaction;	90%
With sodium methylate In methanol at 0℃; for 0.333333h; Product distribution / selectivity;	65%
With sodium methylate In methanol
With sodium acetate In methanol at 20℃;

: ethanimidamide hydrochloride

: 123-06-8
Ethoxymethylenemalononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: ethanimidamide hydrochloride With sodium methylate In ethanol at 20℃; Stage #2: Ethoxymethylenemalononitrile In ethanol for 1h;	74.7%

: 143-37-3
acetamidine

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 109-77-3
malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With dimethyl sulfate at 70℃; for 3.5h; Stage #2: malononitrile With sodium methylate In methanol at -15℃; for 0.666667h; Stage #3: acetamidine In methanol at -15 - 20℃; for 15.5h;	69%

...Expand

: ethanimidamide hydrochloride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 109-77-3
malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With dimethyl sulfate at 70℃; for 3.5h; Stage #2: With sodium methylate In methanol at -20 - -10℃; for 0.666667h; Stage #3: ethanimidamide hydrochloride; malononitrile Further stages;	69%

...Expand

: 38238-93-6
2-diethylaminomethylenemalononitrile

: 124-42-5
acetamidine hydrochloride

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With sodium methylate In methanol at 0℃; for 0.333333h;	63%

: 672-81-1
2-(methoxymethylene)malononitrile

: 143-37-3
acetamidine

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Stage #1: acetamidine With sodium methylate In ethanol at 20℃; for 0.666667h; Stage #2: 2-(methoxymethylene)malononitrile	26%

: 27058-54-4
2-methyl-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With trichlorophosphate folgendes Erhitzen mit aethanol.NH3;
Multi-step reaction with 2 steps 1: POCl3 2: NH3 View Scheme

: 38875-74-0
4-chloro-2-methylpyrimidine-5-carbonitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With ammonia

: 7389-14-2
2-methyl-4-amino-5-(carboxamidemethyl)pyrimidine

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With trichlorophosphate

: 874495-29-1
4-ethoxy-2-methyl-pyrimidine-5-carbonitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With ammonia

: 76574-37-3
4-amino-6-chloro-2-methyl-5-pyrimidinecarbonitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With methanol; Lindlar's catalyst Hydrogenation;

: 64-17-5
ethanol

: 2208-07-3
ethyl acetimidate hydrochloride

: 672-25-3
aminomethylene-malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Versetzen der Reaktionsloesungen mit alkoh.NaOH oder Natriumaethylat-Loesung;

...Expand

: 3613-29-4
thioacetimidic acid ethyl ester

: 672-25-3
aminomethylene-malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 62-55-5
thioacetamide

: 672-25-3
aminomethylene-malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: iminomethyl-malononitrile

: 62-55-5
thioacetamide

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 78-39-7
Triethyl orthoacetate

: 672-25-3
aminomethylene-malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 64-17-5
ethanol

: 143-37-3
acetamidine

: 123-06-8
Ethoxymethylenemalononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

...Expand

: 143-37-3
acetamidine

: 123-06-8
Ethoxymethylenemalononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 56-23-5
tetrachloromethane

: 64-17-5
ethanol

: 2-cyano-3-imino-propionic acid ethyl ester

: 1000-84-6
O-ethyl acetimidate

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Raumtemperatur;
Raumtemperatur;

...Expand

: 1000-84-6
O-ethyl acetimidate

: 123-06-8
Ethoxymethylenemalononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With ammonia
With ammonia

: 1000-84-6
O-ethyl acetimidate

: 672-25-3
aminomethylene-malononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 124-42-5
acetamidine hydrochloride

: 123-06-8
Ethoxymethylenemalononitrile

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
With sodium ethanolate 1) EtOH; 2) EtOH; Yield given. Multistep reaction;
With ethanol; sodium for 2h;
Stage #1: acetamidine hydrochloride With sodium ethanolate In ethanol at 20℃; for 1h; Stage #2: Ethoxymethylenemalononitrile In ethanol at 20℃; for 3h;

: 1000-84-6
O-ethyl acetimidate

: 123-06-8
Ethoxymethylenemalononitrile

alcoholic NH3: alcoholic NH3

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

...Expand

: 2208-07-3
ethyl acetimidate hydrochloride

: 123-06-8
Ethoxymethylenemalononitrile

alcoholic NH3: alcoholic NH3

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

Conditions

Conditions	Yield
Versetzen der Reaktionsloesungen mit alkoh.NaOH oder Natriumaethylat-Loesung;

...Expand

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 95-02-3
5-(aminomethyl)-2-methylpyrimidin-4-amine

Conditions

Conditions	Yield
With ammonia; hydrogen In methanol at 70 - 100℃; under 14251.4 Torr; Reagent/catalyst; Temperature;	100%
With ammonia; hydrogen In methanol at 100℃; under 30003 Torr; for 5h; Autoclave; Saturated solution; Large scale reaction;	98%
With ammonia; hydrogen In methanol at 60℃; under 30003 Torr; for 24h; Autoclave;	90%

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 124-38-9
carbon dioxide

: 112842-89-4
7-methyl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione

Conditions

Conditions	Yield
With 1,5-diazabicyclo[4.3.0]non-5-ene 2,2,2-trifluoroethanol at 90℃; for 48h;	85%
With 1,5-diazabicyclo[4.3.0]non-5-ene 2,2,2-trifluoroethanol at 90℃; under 760.051 Torr; for 48h; Green chemistry;	85%

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 73-68-7
4-amino-2-methylpyrimidine-5-carbaldehyde

Conditions

Conditions	Yield
With formic acid; nickel In water for 0.25h; Reflux;	83%
With formic acid In water for 0.25h; Reflux;	83%
With sulfuric acid; palladium 10% on activated carbon; hydrogen In water at 20℃; for 16h;	70%

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 173557-81-8
4-amino-2-methylpyrimidine-5-carbaldehyde-d

Conditions

Conditions	Yield
With lithium aluminium deuteride In tetrahydrofuran for 1.5h;	28%

: 64-18-6
formic acid

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 73-68-7
4-amino-2-methylpyrimidine-5-carbaldehyde

Conditions

Conditions	Yield
nickel at 80 - 100℃; for 0.75h;	20%

: 97-64-3, 2676-33-7
ethyl 2-hydroxypropionate

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-lactamide

Conditions

Conditions	Yield
With kieselguhr; ethanol; nickel at 140 - 150℃; Hydrogenation.unter Druck;

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 118801-92-6
7-methyl-pyrimido[4,5-d]pyrimidin-4-ylamine

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 1886-34-6
2-methyl-4-amino-5-formylaminomethylpyrimidine

Conditions

Conditions	Yield
With nickel at 130 - 150℃; under 36775.4 - 73550.8 Torr; Hydrogenation;

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

A: 108482-83-3
(4-amino-2-methyl-pyrimidin-5-ylmethyl)-(4-amino-2-methyl-pyrimidin-5-ylmethylen)-amine

B: 1886-34-6
2-methyl-4-amino-5-formylaminomethylpyrimidine

Conditions

Conditions	Yield
With ethanol at 150℃; Hydrogenation;

...Expand

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 113-00-8
guanidine nitrate

: 4,6-bis-(4-amino-2-methyl-pyrimidin-5-yl)-[1,3,5]triazin-2-ylamine

Conditions

Conditions	Yield
With ethanol

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 109-94-4
formic acid ethyl ester

: 1886-34-6
2-methyl-4-amino-5-formylaminomethylpyrimidine

Conditions

Conditions	Yield
With nickel at 130 - 150℃; under 36775.4 - 73550.8 Torr; Hydrogenation;

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 109-94-4
formic acid ethyl ester

A: 108482-83-3
(4-amino-2-methyl-pyrimidin-5-ylmethyl)-(4-amino-2-methyl-pyrimidin-5-ylmethylen)-amine

B: 1886-34-6
2-methyl-4-amino-5-formylaminomethylpyrimidine

Conditions

Conditions	Yield
With nickel at 150℃; Hydrogenation;

...Expand

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 73-67-6
2-methyl-4-amino-5-hydroxymethylpyrimidine

Conditions

Conditions	Yield
With hydrogenchloride; palladium; acetic acid Hydrogenation;
Multi-step reaction with 2 steps 1: 20 percent / Raney Ni / 0.75 h / 80 - 100 °C 2: 93 percent / NaBH4 / methanol / 0.5 h / Ambient temperature View Scheme

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 7389-14-2
2-methyl-4-amino-5-(carboxamidemethyl)pyrimidine

Conditions

Conditions	Yield
With sulfuric acid
With dihydrogen peroxide

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 82302-19-0
4-amino-2-methyl-pyrimidine-5-carbothioic acid amide

Conditions

Conditions	Yield
With hydrogen sulfide
With pyridine; hydrogen sulfide; triethylamine In N-methyl-acetamide

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 769-52-8
4-amino-2-methylpyrimidine-5-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide
With sodium hydroxide
With water; potassium hydroxide

: 698-29-3
2-methyl-4-amino-5-cyanopyrimidine

: 108482-83-3
(4-amino-2-methyl-pyrimidin-5-ylmethyl)-(4-amino-2-methyl-pyrimidin-5-ylmethylen)-amine

Conditions

Conditions	Yield
With nickel Hydrogenation;
Multi-step reaction with 2 steps 1: Raney nickel / Hydrogenation View Scheme

5-Pyrimidinecarbonitrile,4-amino-2-methyl- Specification

The CAS register number of 5-Pyrimidinecarbonitrile,4-amino-2-methyl- is 698-29-3. It also can be called as 2-Methyl-4-amino-5-cyanopyrimidine and the IUPAC name about this chemical is 4-amino-2-methylpyrimidine-5-carbonitrile. The molecular formula about this chemical is C₆H₆N₄ and the molecular weight is 134.14. It belongs to the following product categories which include Pyrimidine; Pyrazines, Pyrimidines & Pyridazines; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides; Pyrazines, Pyrimidines & Pyridazines and so on.

Physical properties about 5-Pyrimidinecarbonitrile,4-amino-2-methyl- are: (1)ACD/LogP: 0.40; (2)ACD/LogD (pH 5.5): 0.39; (3)ACD/LogD (pH 7.4): 0.4; (4)ACD/BCF (pH 5.5): 1.17; (5)ACD/BCF (pH 7.4): 1.18; (6)ACD/KOC (pH 5.5): 38.77; (7)ACD/KOC (pH 7.4): 39.15; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)Polar Surface Area: 52.81Å²; (11)Index of Refraction: 1.582; (12)Molar Refractivity: 35.15 cm³; (13)Molar Volume: 105.3 cm³; (14)Polarizability: 13.93x10^-24cm³; (15)Surface Tension: 75.3 dyne/cm; (16)Enthalpy of Vaporization: 55.69 kJ/mol; (17)Boiling Point: 315.6 °C at 760 mmHg; (18)Vapour Pressure: 0.000432 mmHg at 25°C.

Uses of 5-Pyrimidinecarbonitrile,4-amino-2-methyl-: it can be used to produce 4-amino-2-methyl-pyrimidine-5-carbaldehyde with formic acid at temperature of 80 - 100 ℃. This reaction will need catalyst Raney Ni with reaction time of 45 min. The yield is about 20%.

You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1cnc(nc1N)C
(2)InChI: InChI=1/C6H6N4/c1-4-9-3-5(2-7)6(8)10-4/h3H,1H3,(H2,8,9,10)
(3)InChIKey: YBPNIILOUYAGIF-UHFFFAOYAI
(4)Std. InChI: InChI=1S/C6H6N4/c1-4-9-3-5(2-7)6(8)10-4/h3H,1H3,(H2,8,9,10)
(5)Std. InChIKey: YBPNIILOUYAGIF-UHFFFAOYSA-N

Product Name

4-AMINO-2-METHYLPYRIMIDINE-5-CARBONITRILE

Synthetic route

5-Pyrimidinecarbonitrile,4-amino-2-methyl- Specification

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