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[ CAS No. 91678-81-8 ]

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Chemical Structure| 91678-81-8
Chemical Structure| 91678-81-8
Structure of 91678-81-8 * Storage: {[proInfo.prStorage]}

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Product Details of [ 91678-81-8 ]

CAS No. :91678-81-8 MDL No. :MFCD00107172
Formula : C6H9N3 Boiling Point : 243.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :123.16 g/mol Pubchem ID :-
Synonyms :

Safety of [ 91678-81-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 91678-81-8 ]

  • Downstream synthetic route of [ 91678-81-8 ]

[ 91678-81-8 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 91678-81-8 ]
  • [ 60187-00-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride Diazotization;
  • 2
  • [ 412341-23-2 ]
  • [ 91678-81-8 ]
YieldReaction ConditionsOperation in experiment
With sodium dithionite
YieldReaction ConditionsOperation in experiment
3-Chlor-2,6-dimethylpyrazin, 28percentaq.NH3 (30h 200grad, Autoklav);
(yield)17percent;
3-Iod-2,6-dimethylpyrazin, 28percentaq.NH3 (15h 200grad, Autoklav);
(yield)23percent;

  • 4
  • [ 91678-81-8 ]
  • [ 183610-69-7 ]
  • 3-(4-fluoro-phenyl)-2-(4-methanesulfonyl-phenyl)-6,8-dimethyl-imidazo[1,2-<i>a</i>]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 60℃;
  • 6
  • [ 91678-81-8 ]
  • [ 85-44-9 ]
  • 3,5-dimethyl-2-phthalimidopyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; chlorobenzene 1.a (a) (a) Preparation of 3,5-dimethyl-2-phthalimidopyrazine 481 g of phthalic anhydride were added to a solution of 307 g of 2-amino-3,5-dimethylpyrazine and 1100 g of chlorobenzene at 25° C., and the mixture was heated at the boil for 6 hours, the water of reaction being removed continuously. When the reaction was complete, 1 l of water was added to the resulting brown solution, after which the chlorobenzene was distilled off together with water, while keeping the volume of water constant. A further 0.5 l of water was then added to the remaining aqueous solution, and the mixture was heated to the boil and then cooled to 25°-30° C., the product being precipitated. The mixture obtained was stirred for a further 2 hours at this temperature, after which the product was isolated and taken up in 1.5 l of boiling methanol, the solution was cooled to 0° C. and the product was then filtered off. The yield was virtually quantitative, and the melting point was 142°-143° C.
  • 7
  • [ 91678-81-8 ]
  • [ 1097180-24-9 ]
  • [ 1227852-63-2 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 150℃; for 0.5h; 1 Example 1 6,8-dimethyl-2-({(2S)-1-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-2-piperidinyl}methyl)imidazo[1,2-a]pyrazine (HCl salt) (E1) To a solution of 1,1-dimethylethyl(2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.140 g, 0.44 mmol) in DMF (2 ml) was added 3,5-dimethyl-2-pyrazinamine (0.054 g, 0.44 mmol) and the mixture was stirred at 150° C. for 30 min. The reaction mixture was charged into a SCX column and was eluted with methanol and ammonia 2 M in methanol. Collected fractions gave 0.115 g of a crude containing the desired 6,8-dimethyl-2-[(2S)-2-piperidinylmethyl]imidazo[1,2-a]pyrazine. UPLC: rt=0.34, peak observed: 245 (M+1). C14H20N4 requires 244. Into a 7 ml screw capped vial 2-methyl-5-phenyl-1,3-thiazole-4-carboxylic acid (0.114 g, 0.52 mmol) was dissolved in DCM (1 ml), Oxalyl chloride (0.100 ml, 1.14 mmol) then DMF (0.036 ml, 0.47 mmol) were added and the resulting mixture was stirred for 30 min at rt. The solvent was removed under reduced pressure and the resulting yellow solid dissolved in DCM (1 ml) and added dropwise to the solution containing the crude (0.115 g) 6,8-dimethyl-2-[(2S)-2-piperidinylmethyl]imidazo[1,2-a]pyrazine and TEA (0.197 ml, 0.47 mmol) in DCM (1 ml) cooled at 0° C. The ice-bath was removed and the reaction mixture left under stirring at rt for 1 h. DCM was added and the mixture washed with a saturated NaHCO3 aqueous solution, the organic phase was separated, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica gel (Biotage 25 M, DCM/MeOH, 90/01) and by fraction lynx (basic method). The free base of the title compound was obtained (0.039 g, 0.079 mmol, 20% yield from D2, three steps) as a yellow solid. UPLC: rt=0.58, peak observed: 446 (M+1). C25H27N5OS requires 445. 1H NMR [the product is present as a mixture of conformers (ratio c.ca 60/40)] (500 MHz, DMSO-d6). The free base (0.037 g, 0.08 mmol) was transferred into a 7 ml screw capped vial with anhydrous DCM (1 ml) and the solution cooled to 0° C. HCl (0.125 ml of a 1 M solution in Et2O, 0.13 mmol) was added dropwise and the mixture stirred for 15 min. The solvent was removed under reduced pressure and the resulting solid triturated with anhydrous Et2O. The title compound was obtained (0.041 g, 0.08 mmol, 98% yield) as a white solid. UPLC: rt=0.58, peak observed: 446 (M+1-HCl). C25H28ClN5OS requires 482.
  • 8
  • [ 91678-81-8 ]
  • [ 1097180-24-9 ]
  • [ 13743-09-4 ]
  • [ 1227852-62-1 ]
YieldReaction ConditionsOperation in experiment
20% Example 1: 6,8-dimethyl-2-({(2S)-l-[(2-methyl-5-phenyl-l,3-thiazol-4-yl)carbonyl]-2- piperidinyl}methyl)imidazo[l,2-alpha]pyrazine (HCl salt) (El):To a solution of 1,1-dimethylethyl (25)-2-(3-bromo-2-oxopropyl)-l-piperidinecarboxylate D2 (0.140 g, 0.44 mmol) in DMF (2 ml) was added 3,5-dimethyl-2-pyrazinamine (0.054 g, 0.44 mmol) and the mixture was stirred at 150 0C for 30 min. The reaction mixture was charged into a SCX column and was eluted with methanol and ammonia 2 M in methanol. Collected fractions gave 0.115 g of a crude containing the desired 6,8-dimethyl-2-[(25)-2- piperidinylmethyl]imidazo[l,2-alpha]pyrazine. UPLC: rt = 0.34, peak observed: 245 (M+l). C14H2ON4 requires 244. Into a 7 ml screw capped vial 2-methyl-5-phenyl-l,3-thiazole-4- carboxylic acid (0.114 g, 0.52 mmol) was dissolved in DCM (1 ml), Oxalyl chloride (0.100 ml, 1.14 mmol) then DMF (0.036 ml, 0.47 mmol) were added and the resulting mixture was stirred for 30 min at rt. The solvent was removed under reduced pressure and the resulting yellow solid dissolved in DCM (1 ml) and added dropwise to the solution containing the crude (0.115 g) 6,8-dimethyl-2-[(25)-2-piperidinylmethyl]imidazo[l,2-alpha]pyrazine and TEA (0.197 ml, 0.47 mmol) in DCM (1 ml) cooled at 0 0C. The ice-bath was removed and the reaction mixture left under stirring at rt for 1 h. DCM was added and the mixture washed with a saturated NaHCO3 aqueous solution, the organic phase was separated, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica gel (Biotage 25 M, DCM/MeOH, 90/01) and by fraction lynx (basic method). The free base of the title compound was obtained (0.039 g, 0.079 mmol, 20% yield from D2, three steps) as a yellow solid. UPLC: rt = 0.58, peak observed: 446 (M+l). C25H27N5OS requires 445. 1H NMR [the product is present as a mixture of conformers (ratio c.ca 60/40)] (500 MHz, DMSO-d6). The free base (0.037 g, 0.08 mmol) was transferred into a 7 ml screw capped vial with anhydrous DCM (1 ml) and the solution cooled to 0 0C. HCl (0.125 ml of a 1 M solution in Et2O, 0.13 mmol) was added dropwise and the mixture stirred for 15 min. The solvent was removed under reduced pressure and the resulting solid triturated with anhydrous Et2O. The title compound was obtained (0.041 g, 0.08 mmol, 98% yield) as a white solid. UPLC: rt = 0.58, peak observed: 446 (M+1-HC1). C25H28ClN5OS requires 482.
  • 9
  • [ 91678-81-8 ]
  • [ 1355999-71-1 ]
  • [ 1447364-31-9 ]
YieldReaction ConditionsOperation in experiment
249 mg With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 130℃; for 3h; Molecular sieve; Reflux; Microwave irradiation; Int-2 Intermediate Example lnt-2: ferf-Butyl {1-[4-(6,8-dimethyl-3-phenylimidazo[1,2-a]pyrazin-2-yl)phenyl]- c clobutyl}carbamate Intermediate Example lnt-2: ferf-Butyl {1-[4-(6,8-dimethyl-3-phenylimidazo[1,2-a]pyrazin-2-yl)phenyl]- c clobutyl}carbamate To a mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (770 mg, 1.61 mmol, 1.0 eq), 3,5-dimethylpyrazin-2-amine (CAS-Nr. 91678-81-8, 218 mg, 1.77 mmol, 1.1 eq) and diisopropylethylamine (0.28 mL, 1.61 mmol, 1.0 eq) in 10 mL isopropanol was added 3A molsieves. The reaction mixture was heated to reflux temperature for 2h. No conversion was observed under these conditions (UPLC-MS). Therefore, the reaction mixture was heated to 130 for 1 h under microwave conditions ( single mode microwave oven). The reaction mixture was filtered to remove the molsieve and the filtrate was concentrated in vacuo. The crude mixture was purified via MPLC (Biotage Isolera, 25 g Snap cartridge, DCM -> DCM/ethanol 95/5) to deliver 249 mg (31%) of the title compound. UPLC-MS (Method 1): RT = 1.40 min; m/z = 469 (M+H) +.
  • 10
  • [ 91678-81-8 ]
  • [ 638-07-3 ]
  • [ 1446334-80-0 ]
YieldReaction ConditionsOperation in experiment
78% In ethanol at 100℃; for 16.5h; Inert atmosphere; High pressure;
5 g In ethanol at 100℃; for 16h; 5.2 Part 2: Preparation of ethyl 2-(6,8-dimethylimidazo[l,2-a]pyrazin-2-yl)acetate A 75 mL pressure vessel was charged with ethyl 4-chloro-3-oxo-butyrate (4 g, 24.4 mmol), 3,5-dimethylpyrazin-2-amine (3 g, 24.4 mmol) and 200 proof ethanol (24 mL). After stirring at 100 °C in an oil bath for 16 hours, the reaction mixture was concentrated, diluted with dichloromethane and a saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated, and purified on silica gel. Elution with a gradient mixture of dichloromethane and methanol yielded ethyl 2-(6,8- dimethylimidazo[l,2-a]pyrazin-2-yl)acetate as a light brown solid (5 g). MS m/z 234 [M+H]+.
  • 11
  • [ 91678-81-8 ]
  • [ 1453265-77-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 16 h / 100 °C 2: piperidine; acetic acid / ethanol / 2 h / 150 °C / Microwave irradiation
  • 12
  • [ 91678-81-8 ]
  • [ 1453265-07-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 16 h / 100 °C 2: piperidine; acetic acid / ethanol / 2 h / 150 °C / Microwave irradiation 3: hydrogenchloride / dichloromethane; 1,4-dioxane / 16 h / 20 °C
  • 13
  • [ 91678-81-8 ]
  • [ 1448704-72-0 ]
  • 3-(6,8-dimethylimidazo [1,2-a]pyrazin-2-yl)-7-fluoro-1H-isochromen-1-one hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In acetonitrile at 100℃; Sealed tube; 6.D Preparation of Cpd 65 Step D: The bromoketone intermediate obtained in Step C (1.43 g, 5.0 mmol) was mixed with 3,5-dimethylpyrazin-2-amine (0.67 g, 5.5 mmol) and acetonitrile (10.0 mL) in a sealed tube. The mixture was stirred at 100 °C overnight and cooled to room temperature. Ethyl acetate (20 mL) was added and the precipitate was collected, washed with ethyl acetate and then dried, providing 3-(6,8-dimethylimidazo[l,2-a]pyrazin-2-yl)-7-fluoro-lH-isochromen-l-one hydrobromide (1.81 g, 93%). MS m/z 310.3 [M+H]+.
  • 14
  • [ 91678-81-8 ]
  • [ 1448704-72-0 ]
  • [ 1448703-61-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 100 °C / Sealed tube 2: 1-methyl-pyrrolidin-2-one / 24 h / 180 °C / Inert atmosphere
  • 15
  • [ 91678-81-8 ]
  • [ 1448703-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetonitrile / 100 °C / Sealed tube 2: tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; potassium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 4: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
  • 16
  • [ 91678-81-8 ]
  • BrH*C27H28N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 100 °C / Sealed tube 2: tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; potassium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere
  • 17
  • [ 91678-81-8 ]
  • [ 1448703-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetonitrile / 100 °C / Sealed tube 2: tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; potassium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 18
  • [ 91678-81-8 ]
  • [ 1448704-80-0 ]
  • [ 1448704-81-1 ]
YieldReaction ConditionsOperation in experiment
80% In acetonitrile at 100℃; Sealed tube; 12.2.D Part 2, Step D: The intermediate obtained in Part 2, Step C (4.84 g, 14.0 mmol) was mixed with 3,5-dimethylpyrazin-2-amine (1.81 g, 14.7 mmol), obtained in Part 1, and acetonitrile (30 mL) in a sealed tube. The mixture was stirred at 100 °C overnight and cooled to room temperature. Ethyl acetate (60 mL) was added and the precipitate was collected, then washed with ethyl acetate and dried, providing 3-(6,8-dimethylimidazo[l,2-a]pyrazin-2-yl)-7- bromo-lH-isochromen-l-one hydrobromide (5.04 g, 80%). MS m/z 370.2, 372.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.50-8.54 (1H, m), 8.34 (1H, s), 8.21 (1H, d, J=1.89 Hz), 8.02 (1H, dd, J=8.35, 2.05 Hz), 7.80 (1H, d, J=8.51 Hz), 7.51-7.57 (1H, m), 2.79 (3H, s), 2.41 (3H, d, J=0.95 Hz).
  • 19
  • [ 108-50-9 ]
  • [ 91678-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuryl dichloride / N,N-dimethyl-formamide / 2.5 h / 60 °C / Cooling with ice 2: copper(II) oxide; ammonium hydroxide / 72 h / 150 °C / Sealed tube
  • 20
  • [ 38557-72-1 ]
  • [ 91678-81-8 ]
YieldReaction ConditionsOperation in experiment
84% With ammonium hydroxide; copper(II) oxide; at 150℃; for 72.0h;Sealed tube; Part 1, Step B: A mixture of <strong>[38557-72-1]2-chloro-3,5-dimethylpyrazine</strong> (28.5 g, 0.2 mol), prepared above, CuO (0.8 g, 0.01 mol) and concentrated aqueous NH3 (28-30 %, 150 mL) was stirred in a sealed pressure vessel at 150 C for 3 days. After cooling, the mixture was concentrated to dryness and the residue was treated with ethyl acetate (500 mL), then stirred for 15 minutes and filtered. The precipitate was washed with additional ethyl acetate (about 1.5 L) until the starting material was no longer detected in the filtrate. The filtrates were combined and concentrated. The residue was chromatographed on a silica gel column (MeOH/CH2Cl2, 0-10%) to furnish a yellow/brownish solid (20.7 g, 84%). 1H NMR (500 MHz, CHLOROFORM-^) delta ppm 7.68 (1H, s), 2.46 (3H, s), 2.42 (3H, d, J=0.63 Hz).
  • 21
  • [ 91678-81-8 ]
  • [ 70-23-5 ]
  • ethyl 6,8-dimethylimidazo[1,2-a]pyrazine-2-carboxylate hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.3% In 1,2-dimethoxyethane at 0 - 20℃; for 2h; B.1.a.1 a) step1 : Ethyl 6,8-dimethylimidazo[l,2-a]pyrazine-2-carboxylate hydrobromide a) step1 : Ethyl 6,8-dimethylimidazo[l,2-a]pyrazine-2-carboxylate hydrobromide To a solution of 3,5-dimethylpyrazin-2-amine (200 mg, 1.62 mmol) in DME (6.00 ml) was added ethyl3-bromo-2-oxopropanoate (380 mg, 245 f..Ll, 1.95 mmol) at 0°C. The mixture wasstirred for 2 hours at room temperature. The suspension was filtered and washed withdimethoxyethane. The filtrate was taken in ethanol ( 4 ml) and refluxed for 1.5 hours. Thereaction mixture was cooled to room temperature, filtered and washed with ethanol to provide 323 mg (66.3 %) of the title compound as a light yellow solid. MS (m/e): 220.1 (M+H+)
  • 22
  • [ 91678-81-8 ]
  • 7-bromo-3-(2-bromoacetyl)-2H-chromen-2-one [ No CAS ]
  • 7-bromo-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In acetonitrile at 90℃; for 4h;
88% In acetonitrile at 90℃; for 4h; 48.A Step A: A mixture of 7-bromo-3-(2-bromoacetyl)-2H-chromen-2-one (2.0 g, 5.78 mmol, prepared in Example 37, Step B), 2-amino-3,5-dimethylpyrazine (825 mg, 6.71 mmol) and CH3CN (22 mL) was heated at 90° C. for 4 h. The addition of an aqueous saturated NaHCO3 solution to the mixture resulted in the formation of a precipitate. The precipitate was collected by vacuum filtration and triturated with 1:1 hexane/acetone, yielding 7-bromo-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-2H-chromen-2-one (1.9 g, 88%) as an orange solid. 1H NMR (500 MHz, DMSO-d6): δ 8.81 (1H, s), 8.61 (1H, s), 8.31 (1H, s), 7.93 (1H, d, J=8 Hz), 7.76 (1H, d, J=1.5 Hz), 7.58 (1H, dd, J=8 Hz, 1.5 Hz), 2.76 (3H, s), 2.37 (3H, s).
  • 24
  • [ 91678-81-8 ]
  • [ 1446333-79-4 ]
  • 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-fluoro-2H-chromen-2-one hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In acetonitrile at 120℃; for 0.333333h; Sealed tube;
90% In acetonitrile at 120℃; for 0.333333h; Sealed tube; 43.A Step A: A mixture of 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (0.684 g, 2.4 mmol, prepared in Example 36, Part 2) and 3,5-dimethylpyrazin-2-amine (0.246 g, 2.0 mmol) in CH3CN (10 mL) was stirred at 120° C. in a sealed tube for 20 min. The mixture was cooled to room temperature and diluted with Et2O to produce a precipitate. The solid was collected by vacuum filtration, washed with Et2O and dried to give 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-fluoro-2H-chromen-2-one hydrobromide (0.7 g, 90%) as a tan solid. MS m/z 310.1 [M+H]+.
  • 25
  • [ 91678-81-8 ]
  • tert-butyl 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,2-dimethoxyethane / 0.75 h / 20 °C 1.2: 3 h / 90 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 1.5 h / -50 °C / Inert atmosphere
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