4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With methanol; palladium(II) hydroxide at 20℃; for 48h; | 98% |
With hydrogen; palladium(II) hydroxide In methanol at 20℃; under 760.051 Torr; for 48h; | 98% |
2-chloro-4,6-dimethoxypyrimidine
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With ammonia In tetrahydrofuran; water at 100 - 110℃; for 4h; Solvent; Autoclave; Large scale; | 96.3% |
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Reagent/catalyst; Inert atmosphere; | 80% |
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 96 h / Reflux 2: methanol; palladium(II) hydroxide / 48 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 96 h / Reflux 2: hydrogen; palladium(II) hydroxide / methanol / 48 h / 20 °C / 760.05 Torr View Scheme |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
Stage #1: 3-amino-3-methoxy-N-nitrile-2-propionamidine With acetic acid In toluene at 150℃; for 3h; Industrial scale; Stage #2: In toluene Reagent/catalyst; Temperature; Industrial scale; | 96% |
With acetic acid at 120 - 130℃; for 4h; Reagent/catalyst; Large scale; | 95.47% |
In toluene at 100℃; for 5h; | 82.06% |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With hydrogenchloride In water at 40 - 45℃; for 4h; Temperature; | 91.3% |
Conditions | Yield |
---|---|
Stage #1: methanol With sodium hydride In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: 2-Amino-4,6-dichloropyrimidine In tetrahydrofuran for 15h; Inert atmosphere; | 91% |
With sodium for 13h; Reflux; | 85% |
With sodium at 20℃; for 85h; Reflux; | 85% |
With sodium |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With hydrogenchloride In water at 60 - 65℃; for 3h; | 90.6% |
CYANAMID
dimethyl 1,3-propanediimidate dihydrochloride
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In water; toluene | 90% |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
Stage #1: methyl 3-amino-3-methoxy-N-nitrile-2-propionamidine With zinc(II) chloride In toluene at 65℃; for 3h; Stage #2: With hydrogenchloride In toluene at 20℃; for 2h; Solvent; Reagent/catalyst; Temperature; | 90% |
at 105℃; for 7h; Temperature; | 80% |
In methanol for 6h; Solvent; Reflux; | 125g |
CYANAMID
dimethyl 1,3-propanediimidate dihydrochloride
4-methyl-2-pentanone
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In water | 89.8% |
dimethyl 1,3-propanediimidate dihydrochloride
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In water; toluene | 89.3% |
diazomethane
2-aminopyrimidine-4,6-diol
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In methanol; diethyl ether at 20℃; for 24h; | 86% |
In methanol; diethyl ether at 20℃; for 24h; | 86% |
2-Amino-4,6-dichloropyrimidine
sodium methylate
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With methanol | |
With methanol; xylene | |
In methanol at 20℃; Substitution; |
A
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With sodium hydroxide at 50℃; Rate constant; Thermodynamic data; effect of acidic conditions (pH 1.4-5.6); effect of temperatures(40-50 deg C); ΔH*; ΔS*; effect of ionic strength on alkaline hydrolysis of title comp.; | |
With iron oxide; water at 25℃; pH=4.8; Kinetics; Further Variations:; Reagents; |
methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifluoromethyl)-3-pyridinecarboxylate monosodium salt
A
4,6-dimethoxy-2-aminopyrimidine
B
methyl 2-(aminosulfonyl)-6-(trifluoromethyl)-3-pyridinecarboxylate
Conditions | Yield |
---|---|
With acetate buffer at 20℃; for 720h; pH=5; Product distribution; Kinetics; Further Variations:; Temperatures; Hydrolysis; rearrangement; |
Conditions | Yield |
---|---|
at 30℃; Kinetics; |
Conditions | Yield |
---|---|
at 30℃; Kinetics; |
nicosulfuron
A
4,6-dimethoxy-2-aminopyrimidine
B
N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; citric acid at 30℃; pH=4; Kinetics; Further Variations:; pH-values; |
dimethyl 1,3-propanediimidate
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile |
dimethyl 1,3-propanediimidate dihydrochloride
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In toluene |
A
4,6-dimethoxy-2-aminopyrimidine
B
6-amino-5-[(4,6-dimethoxypyrimidin-2-yl)methylamino]-1,5,6,8-tetrahydro-7-oxa-8λ6-tia-1,2,5,6-tetraaza-azulen-4-one
Conditions | Yield |
---|---|
In water; acetonitrile for 24h; Irradiation; |
A
4,6-dimethoxy-2-aminopyrimidine
B
N-[[(5-hydroxy-4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide
Conditions | Yield |
---|---|
With iron(III) oxide In water Irradiation; |
2-aminopyrimidine-4,6-diol
carbonic acid dimethyl ester
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 150℃; Temperature; Time; Reagent/catalyst; Concentration; |
amidosulfuron
A
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In water at 30℃; Irradiation; |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene at 110 - 120℃; for 0.5h; Solvent; Temperature; | 285 g |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In toluene Reflux; | 98.4% |
4,6-dimethoxy-2-aminopyrimidine
nicosulfuron
Conditions | Yield |
---|---|
With calcium chloride In toluene Autoclave; Heating; Large scale; | 98.4% |
With tetrabutyl phosphonium bromide In acetonitrile at 60 - 100℃; for 5h; Reagent/catalyst; | 97.13% |
In toluene for 0.5h; Reflux; | 75.6% |
4,6-dimethoxy-2-aminopyrimidine
amidosulfuron
Conditions | Yield |
---|---|
In chlorobenzene | 97.2% |
4,6-dimethoxy-2-aminopyrimidine
2-bromoanisole
4,6-dimethoxy-2-[(2-methoxyphenyl)amino]pyrimidine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 95℃; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
In toluene | A n/a B 96.4% |
bromobenzene
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 95℃; Reagent/catalyst; Solvent; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; | 96% |
4,6-dimethoxy-2-aminopyrimidine
nicosulfuron
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 5h; Temperature; Large scale; | 95.47% |
4,6-dimethoxy-2-aminopyrimidine
N-[(N'-methyl-N'-methylsulfonyl-aminosulfonyl)-aminocarbonyl]-morpholine
amidosulfuron
Conditions | Yield |
---|---|
In toluene | 95% |
4,6-dimethoxy-2-aminopyrimidine
p-methoxybenzyl chloride
4,6-dimethoxy-N,N-bis(4-methoxybenzyl)pyrimidin-2-amine
Conditions | Yield |
---|---|
Stage #1: 4,6-dimethoxy-2-aminopyrimidine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 20℃; | 95% |
Stage #1: 4,6-dimethoxy-2-aminopyrimidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; | 95% |
4,6-dimethoxy-2-aminopyrimidine
1,3-dibromobenzene
2-[(3-bromophenyl)amino]-4,6-dimethoxypyrimidine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 95℃; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; | 94% |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
Stage #1: 4,6-dimethoxy-2-aminopyrimidine; C10H8INO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate | 94% |
4,6-dimethoxy-2-aminopyrimidine
mercaptoacetic acid
4-cyanobenzaldehyde
4-(3-(4,6-dimethoxypyrimidin-2-yl)-4-oxothiazolidin-2-yl)benzonitrile
Conditions | Yield |
---|---|
In toluene Reflux; Dean-Stark; | 93.1% |
4,6-dimethoxy-2-aminopyrimidine
A
N-methylmethane sulphonamide
B
amidosulfuron
Conditions | Yield |
---|---|
In chlorobenzene | A n/a B 92.7% |
4,6-dimethoxy-2-aminopyrimidine
sodium isocyanate
2-sulfonyl chloride-N,N-dimethylnicotinamide
nicosulfuron
Conditions | Yield |
---|---|
Stage #1: sodium isocyanate; 2-sulfonyl chloride-N,N-dimethylnicotinamide With triethylamine In acetonitrile at 25℃; for 5h; Stage #2: 4,6-dimethoxy-2-aminopyrimidine In acetonitrile at 0 - 40℃; for 1h; Temperature; | 92.1% |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In benzene for 4h; Heating; | 92% |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In n-heptane; o-xylene at 90℃; under 337.534 Torr; for 12h; | 91.9% |
In toluene for 4h; Product distribution / selectivity; Heating / reflux; |
4,6-dimethoxy-2-aminopyrimidine
Ethoxycarbonyl isothiocyanate
5,7-dimethoxy-[1,2,4]-triazolo-[1,5-a]-pyrimidin-2-amine
Conditions | Yield |
---|---|
Stage #1: 4,6-dimethoxy-2-aminopyrimidine; Ethoxycarbonyl isothiocyanate In ethyl acetate at 78℃; for 5.33333h; Heating / reflux; Stage #2: With hydroxyammonium sulfate In water; ethyl acetate at 71℃; Heating / reflux; Stage #3: With sodium carbonate In water; ethyl acetate at 71℃; for 7h; pH=6.5 - 7.0; Heating / reflux; | 91.1% |
4,6-dimethoxy-2-aminopyrimidine
3-methoxyphenyl bromide
4,6-dimethoxy-2-[(3-methoxyphenyl)amino]pyrimidine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 95℃; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; | 91% |
4,6-dimethoxy-2-aminopyrimidine
2,6-difluorobenzaldehyde
mercaptoacetic acid
2-(2,6-difluorophenyl)-3-(4,6-dimethoxypyrimidin-2-yl)thiazolidin-4-one
Conditions | Yield |
---|---|
In toluene Reflux; Dean-Stark; | 90.2% |
4,6-dimethoxy-2-aminopyrimidine
Conditions | Yield |
---|---|
In ethanol; toluene Reflux; | 90.1% |
4,6-dimethoxy-2-aminopyrimidine
carbon monoxide
3-trifluoromethylnitrobenzene
Conditions | Yield |
---|---|
With triethylamine; selenium(IV) oxide In toluene at 140 - 150℃; under 22501.8 Torr; for 4h; | 89.8% |
The 2-Amino-4,6-dimethoxypyrimidine with the cas number 36315-01-2, is also called (4,6-Dimethoxypyrimidin-2-amine named by IUPAC. 2-Amino-4,6-dimethoxypyrimidine belongs to the following product categories: (1)Pyridines ; (2)Pyrimidines ; (3)Purines and Pteredines; (4)Pyrimidine; (5)Amines; (6)Pyrimidines; (7)Building Blocks; (8)Heterocyclic Building Blocks.
Properties of 2-Amino-4,6-dimethoxypyrimidine: (1)H bond acceptors: 5 ; (2)H bond donors: 2 ; (3)Freely Rotating Bonds: 2 ; (4)Polar Surface Area: 47.48 Å ; (5)Index of Refraction: 1.547 ; (6)Molar Refractivity: 40.02 cm3 ; (7)Molar Volume: 126.1 cm3 ; (8)Polarizability: 15.86× 10-24cm3 ; (9)Surface Tension: 49.5 dyne/cm ; (10)Density: 1.229 g/cm3 ; (11)Flash Point: 169.4 °C ; (12)Enthalpy of Vaporization: 60.17 kJ/mol ; (13)Boiling Point: 356.4 °C at 760 mmHg ; (14)Vapour Pressure: 2.92E-05 mmHg at 25°C
Uses of 2-Amino-4,6-dimethoxypyrimidine: This product is a kind of important pesticide intermediates for synthesis of sulfonylurea pesticide, such as bensulfuron methyl , Nicosulfuron , cyclosulfamuron , Ethoxysulfuron , Rimsulfuron , Azimsulfuron and so on.
Preparation of 2-Amino-4,6-dimethoxypyrimidine: (1)It is mainly produced by raw materials such as propylene nitriles, methanol, cyanamide. (2) Reaction of N,N-Dimethylaniline, with 2-Amino-4,6-dihydroxypyrimidine and phosphorus oxychloride to produce 2-Amino-4,6-dichloropyrimidine. Then react with sodium methoxide to obtain 2-Amino-4,6-dimethoxypyrimidine.
When you are using this chemical, please be cautious about it as the following:
Firstly, 2-Amino-4,6-dimethoxypyrimidine is irritating not only to eyes, respiratory system but also is irritating to skin. When using it, please wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure :
1. SMILES: O(c1nc(nc(OC)c1)N)C
2. InChI: InChI=1/C6H9N3O2/c1-10-4-3-5(11-2)9-6(7)8-4/h3H,1-2H3,(H2,7,8,9)
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