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2-Amino-4,6-dimethoxypyrimidine

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Name

2-Amino-4,6-dimethoxypyrimidine

EINECS 252-969-6
CAS No. 36315-01-2 Density 1.229 g/cm3
PSA 70.26000 LogP 0.65720
Solubility N/A Melting Point 94-96 °C(lit.)
Formula C6H9N3O2 Boiling Point 356.4 °C at 760 mmHg
Molecular Weight 155.156 Flash Point 169.4 °C
Transport Information N/A Appearance crystalline powder
Safety 26-36/37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 36315-01-2 (2-Amino-4,6-dimethoxypyrimidine) Hazard Symbols IrritantXi
Synonyms

4,6-Dimethoxypyrimidin-2-amine;2-Amino-4,6-dimethoxypyridine;2-Amino-4,6-methoxy pyrimidine;4,6-Dimethoxy-pyrimidin-2-ylamine;2-amino-4,6-dimethoxy pyrimidine(ADMP);

Article Data 45

2-Amino-4,6-dimethoxypyrimidine Synthetic route

N-benzyl-2-amino-4,6-dimethoxypyrimidine

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
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%
13223-25-1

2-chloro-4,6-dimethoxypyrimidine

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
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

3-amino-3-methoxy-N-nitrile-2-propionamidine

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
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%

C9H13N3O2

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
With hydrogenchloride In water at 40 - 45℃; for 4h; Temperature;91.3%
67-56-1

methanol

56-05-3

2-Amino-4,6-dichloropyrimidine

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
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

C10H15N3O2

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
With hydrogenchloride In water at 60 - 65℃; for 3h;90.6%

potassium bicarbonate

420-04-2

CYANAMID

71160-05-9

dimethyl 1,3-propanediimidate dihydrochloride

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
In water; toluene90%

methyl 3-amino-3-methoxy-N-nitrile-2-propionamidine

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
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

potassium bicarbonate

420-04-2

CYANAMID

71160-05-9

dimethyl 1,3-propanediimidate dihydrochloride

108-10-1

4-methyl-2-pentanone

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
In water89.8%

potassium bicarbonate

71160-05-9

dimethyl 1,3-propanediimidate dihydrochloride

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

Conditions
ConditionsYield
In water; toluene89.3%

2-Amino-4,6-dimethoxypyrimidine Specification

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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