Alternatived Products of [ 5521-57-3 ]
Product Details of [ 5521-57-3 ]
CAS No. : 5521-57-3
MDL No. : MFCD00190581
Formula :
C6 H7 N3 O
Boiling Point : -
Linear Structure Formula : -
InChI Key : OYBQCUZBVHFPBU-UHFFFAOYSA-N
M.W : 137.14 g/molPubchem ID : 2760054
Synonyms :
Calculated chemistry of [ 5521-57-3 ]
Physicochemical Properties
Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.09
TPSA : 68.87 Ų
Pharmacokinetics
GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.31 cm/s
Lipophilicity
Log Po/w (iLOGP) : 1.08
Log Po/w (XLOGP3) : -0.25
Log Po/w (WLOGP) : -0.12
Log Po/w (MLOGP) : -1.28
Log Po/w (SILICOS-IT) : 0.47
Consensus Log Po/w : -0.02
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55
Water Solubility
Log S (ESOL) : -0.91
Solubility : 16.8 mg/ml ; 0.123 mol/l
Class : Very soluble
Log S (Ali) : -0.74
Solubility : 25.1 mg/ml ; 0.183 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.6
Solubility : 3.45 mg/ml ; 0.0252 mol/l
Class : Soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7
Application In Synthesis of [ 5521-57-3 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Upstream synthesis route of [ 5521-57-3 ] Downstream synthetic route of [ 5521-57-3 ]
2
[ 5521-55-1 ]
[ 5521-57-3 ]
Yield Reaction Conditions Operation in experiment
With methanol folgende Umsetzung mit NH3 ;
Multi-step reaction with 2 steps
1: sulfuric acid / 8 h / 0 - 65 °C
2: ammonia / methanol / 4 h / 0 - 5 °C
Reference：
[1]Weijlard et al.
[Journal of the American Chemical Society, 1945, vol. 67, p. 802,804]
[2]KomReddy, Venugopal; Rillema, D. Paul; Nguyen, Huy; Kadel, Lava
[Journal of Heterocyclic Chemistry, 2019, vol. 56, # 3, p. 972 - 979]
3
[ 5521-57-3 ]
[ 51037-25-3 ]
Yield Reaction Conditions Operation in experiment
With dihydrogen peroxide; acetic acid at 70℃; for 6h;
With formic acid; dihydrogen peroxide at 40 - 50℃; for 4h; Yield given;
Reference：
[1]Ambrogi; Cozzi; Sanjust; et al.
[European Journal of Medicinal Chemistry, 1980, vol. 15, # 2, p. 157 - 163]
[2]Sato, Nobuhiro; Suzuki, Hiroko
[Journal of Heterocyclic Chemistry, 1993, vol. 30, # 3, p. 841 - 844]
Yield Reaction Conditions Operation in experiment
Hofmann'scher Abbau der Verb. liefert das 2-Amin;
Yield Reaction Conditions Operation in experiment
C6H6N2O2 1. Tributylamin, Dioxan, Aethylchlorformiat (5-6grad) 2. (9-10grad) 3. ges.Lsg.von NH3 in Dioxan (5grad) 4. (20grad, 3h);
2-Carboxy-5-methylpyrazin 1. Ethylchlorformiat, in Dioxan, NBu3 2. NH3 in Dioxan;
Isomerengemisch von 2-Methyl-5(bzw. 6)-carboxymethylpyrazin, NH3;
6
[ 123-32-0 ]
[ 290-37-9 ]
[ 98-96-4 ]
[ 5521-57-3 ]
[ 41110-27-4 ]
Yield Reaction Conditions Operation in experiment
1: 32%
2: 51%
3: 5%
4: 2%
With ammonium hydroxide; air at 400℃;
7
[ 5521-57-3 ]
[ 74416-38-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: borontrifluoride etherate / 6 h / Heating
8
[ 5521-57-3 ]
[ 51037-35-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: borontrifluoride etherate / 6 h / Heating
9
[ 5521-57-3 ]
[ 74416-43-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: borontrifluoride etherate / 6 h / Heating
10
[ 5521-57-3 ]
[ 74416-40-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: borontrifluoride etherate / 6 h / Heating
11
[ 5521-57-3 ]
[ 74416-39-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: borontrifluoride etherate / 6 h / Heating
12
[ 5521-57-3 ]
[ 74416-41-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: borontrifluoride etherate / 6 h / Heating
13
[ 5521-57-3 ]
[ 74416-25-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: 1.)Pivaloyl chloride, (Et)3N / 1.)CH3 Cl -10 deg C; 2.)-10 deg C to room temp., 5 h.
14
[ 5521-57-3 ]
[ 74416-42-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
3: triethylamine / ethyl acetate / Ambient temperature
15
[ 5521-57-3 ]
[ 51037-30-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: H2 O2 , AcOH / 6 h / 70 °C
2: aqu. NaOH / 0.5 h / Heating
16
[ 5521-57-3 ]
[ 156-43-4 ]
N'-(4-ethoxyphenyl)-5-methylpyrazine-2-carboxamidine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
80%
With trimethylaluminum In toluene at 110℃; for 3h; Inert atmosphere;
17
[ 41110-33-2 ]
[ 5521-57-3 ]
18
[ 5521-57-3 ]
[ 98006-90-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
19
[ 5521-57-3 ]
2-(tributylstannyl)-5-methylpyrazine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
3.1: n-butyllithium / diethyl ether; hexane / 2 h / -78 °C / Inert atmosphere; Schlenk technique
3.2: 16 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
20
[ 5521-57-3 ]
5-methyl-2,2'-bipyrazine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
3.1: n-butyllithium / diethyl ether; hexane / 2 h / -78 °C / Inert atmosphere; Schlenk technique
3.2: 16 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
4.1: tetrakis(triphenylphosphine) palladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 120 °C / Inert atmosphere
21
[ 5521-57-3 ]
2-methyl-5-(2-pyridinyl)pyrazine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
3.1: n-butyllithium / diethyl ether; hexane / 2 h / -78 °C / Inert atmosphere; Schlenk technique
3.2: 16 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
4.1: tetrakis(triphenylphosphine) palladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 120 °C / Inert atmosphere
22
[ 5521-57-3 ]
[ 37830-10-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
3.1: tetrakis(triphenylphosphine) palladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 120 °C / Inert atmosphere
Multi-step reaction with 4 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
3.1: n-butyllithium / diethyl ether; hexane / 2 h / -78 °C / Inert atmosphere; Schlenk technique
3.2: 16 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
4.1: tetrakis(triphenylphosphine) palladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 120 °C / Inert atmosphere
Reference：
[1]KomReddy, Venugopal; Rillema, D. Paul; Nguyen, Huy; Kadel, Lava
[Journal of Heterocyclic Chemistry, 2019, vol. 56, # 3, p. 972 - 979]
[2]KomReddy, Venugopal; Rillema, D. Paul; Nguyen, Huy; Kadel, Lava
[Journal of Heterocyclic Chemistry, 2019, vol. 56, # 3, p. 972 - 979]
23
[ 5521-57-3 ]
[2,2'-bipyrazine]-5,5'-dicarboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
3.1: tetrakis(triphenylphosphine) palladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 120 °C / Inert atmosphere
4.1: sulfuric acid; potassium dichromate / 40 - 80 °C
Multi-step reaction with 5 steps
1.1: potassium hydroxide; bromine / water / 0 - 90 °C
2.1: hydrogen bromide / water / 25 - 30 °C
2.2: 1 h / -50 °C
2.3: 1.5 h / -50 °C
3.1: n-butyllithium / diethyl ether; hexane / 2 h / -78 °C / Inert atmosphere; Schlenk technique
3.2: 16 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
4.1: tetrakis(triphenylphosphine) palladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 120 °C / Inert atmosphere
5.1: sulfuric acid; potassium dichromate / 40 - 80 °C
Reference：
[1]KomReddy, Venugopal; Rillema, D. Paul; Nguyen, Huy; Kadel, Lava
[Journal of Heterocyclic Chemistry, 2019, vol. 56, # 3, p. 972 - 979]
[2]KomReddy, Venugopal; Rillema, D. Paul; Nguyen, Huy; Kadel, Lava
[Journal of Heterocyclic Chemistry, 2019, vol. 56, # 3, p. 972 - 979]
24
[ 88394-05-2 ]
[ 5521-57-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: trichlorophosphate; <i>N</i>,<i>N</i>-dimethyl-aniline / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 130 °C
2: 5%-palladium/activated carbon; hydrogen; triethylamine / methanol / 10 h / 20 - 100 °C / 15001.5 Torr / Autoclave
3: dihydrogen peroxide; sodium hydroxide monohydrate / water / 1 h / 55 - 60 °C / pH 8 - 9
25
[ 181284-14-0 ]
[ 5521-57-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 5%-palladium/activated carbon; hydrogen; triethylamine / methanol / 10 h / 20 - 100 °C / 15001.5 Torr / Autoclave
2: dihydrogen peroxide; sodium hydroxide monohydrate / water / 1 h / 55 - 60 °C / pH 8 - 9
26
[ 98006-91-8 ]
[ 5521-57-3 ]
Yield Reaction Conditions Operation in experiment
64 g
With sodium hydroxide monohydrate; dihydrogen peroxide In water at 55 - 60℃; for 1h;
1-3 Preparation of 5-methyl-2-amide pyrazine
Add 68g of the crude product obtained in the previous step to a 1L flask,Add 200ml water, 100ml mass fraction is 30% hydrogen peroxide,100g 20wt% sodium hydroxide aqueous solution was added dropwise to the reaction solution,Ensure that the pH of the reaction solution is between 8-9,Control the dripping rate and keep the temperature between 55-60.After the dropwise addition of sodium hydroxide solution is completed, react at 55°C for 1 hour;Extract twice with 150ml dichloromethane, combine the organic phases, remove the solvent,64 g of product was obtained with a yield of 85.3%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
Life Science
For Research Only
100K+ Compounds
Competitive Price
1-2 Day Shipping
