110223-15-9|2-Amino-3-benzyloxypyrazine| Ambeed

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Quality Control of [ 110223-15-9 ] Purity: 97% SDS Specification

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Product Details of [ 110223-15-9 ]

CAS No. :	110223-15-9
Formula :	C₁₁H₁₁N₃O
M.W :	201.23
SMILES Code :	NC1=NC=CN=C1OCC2=CC=CC=C2
MDL No. :	MFCD09838954
InChI Key :	QKEQFJXWHGVJJU-UHFFFAOYSA-N
Pubchem ID :	13900234

Safety of [ 110223-15-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 110223-15-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	12
Fraction Csp3	0.09
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	57.42
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	61.03 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.82
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.23
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.49
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.82
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.59
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.26
Solubility	1.11 mg/ml ; 0.00554 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.11
Solubility	1.56 mg/ml ; 0.00778 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.96
Solubility	0.022 mg/ml ; 0.000109 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.65 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.48

Application In Synthesis of [ 110223-15-9 ]

* 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.

Downstream synthetic route of [ 110223-15-9 ]

[ 110223-15-9 ] Synthesis Path-Downstream 1~27

1
[ 6863-73-6 ]
[ 100-51-6 ]
[ 110223-15-9 ]

Yield	Reaction Conditions	Operation in experiment
82%		Benzyl alcohol (4.55 g, 42.15 mmol) was added under an inert atmosphere dropwise to a suspension of sodium hydride (1. 01 g, 42.13 mmol, 80%) in N-methylpyrrolidinone. Stirring of the reaction mixture was continued for 30 min. 2-Amino-3-chloropyrazine (Compound I in Scheme 1, 5.0 g, 38.6 mmol) was then added in incrememtal portions and the resultant mixture was heated at 80 C for 24 h. The reaction mixture was subsequently cooled and water (200 mL) was added. The aqueous solution was extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with water (2 x 100 mL), dried (Mg04), and concentrated under reduced pressure to obtain a light brown residue. Addition of cold water to the residue, triggered crystallization of the desired product. The crystals were collected and dried over P2O5 (6.33 g, 82%). 1H-NMR (CDCl3) No. 7. 54 (d, J 3.1 Hz, 1H), 7.45-7. 32 (m, 6H), 5. 38 (s, 2H), 4. 78 (br s, 2H); MS (ESI) 202.2 ([M+H] +)
53.76%		Sodium hydride (188.6 mg, 4.72 mmol) in N, N- dimethylformamide (3 mL) was slowly added dropwise at room temperature and benzyl alcohol was dissolved in it and it was stirred at room temperature for 1 hour. It was added dropwise slowly to a mixture of 2-amino-3-chloro-pyrazine and heating at 100 C refluxed for 15 hours. After cooling the reaction to room temperature and the solvent was evaporated under reduced pressure and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filter and concentrate under reduced pressure . By separation and purification of the residue by column chromatography (ethyl acetate / n-hexane = 1/4) to obtain the objective compound 300 mg at a yield of 53.76%.
53.8%		General procedure: Sodium hydride (60% in mineral oil, 0.04 g, 1 mmol) was addedto a stirred solution of benzyl alcohol derivative (1 mmol) inanhydrous N,N-dimethylformamide (3 mL of DMF) at room temperatureand stirring was continued for 1 h. 2-Amino-3-chloropyrazine (8b, 0.13 g, 1 mmol) was added to the reactionmixture and the reaction mixture was stirred at 100 C for 15 h.After cooling, the solvent was evaporated and the residue waspartitioned betweenwater and dichloromethane. The organic layer was dried over sodium sulfate anhydrous, filtered, and concentrated.The residue was purified by column chromatography (SiO2,EA/n-Hex 1/5). 4.1.2.1 3-(Benzyloxy)pyrazin-2-amine (9g) Yellow solid, yield: 53.8%, 1H NMR (400?MHz, CDCl3) delta?=?5.45 (2H, s, OCH2Ph), 6.20 (2H, br, NH2), 7.38-7.48 (7H, m, ArH). Reported [ 48,49].

General procedure: NaH (60% in mineral oil, 0.04 g, 1 mmol) was added to a stirredsolution of the appropriate benzyl alcohol derivative (1 mmol) inanhydrous DMF (3 mL) at room temperature and stirring wascontinued for 1 h. Commercially available 2-amino-3-chloropyrazine (0.13 g, 1 mmol) was added to the reactionmixture which was further stirred at 100 C for 15 h. After cooling,the solvent was evaporated and the residue was partitioned betweenwater and dichloromethane. The organic layer was driedover anhydrous Na2SO4, filtered, and concentrated. The residuewaspurified by flash column chromatography (SiO2, EA/n-Hex 1/5).

References: [1]Patent: WO2005/34837,2005,A2 .Location in patent: Page/Page column 43-44.
[2]Patent: KR101481952,2015,B1 .Location in patent: Paragraph 0797; 0798.
[3]European Journal of Medicinal Chemistry,2018,vol. 144,p. 529 - 543.
[4]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.
[5]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.
[6]MedChemComm,2014,vol. 5,p. 333 - 337.
[7]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

2
[ 6863-73-6 ]
[ 100-51-6 ]
[ 110223-15-9 ]
[ 132972-99-7 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

3
[ 15568-85-1 ]
[ 110223-15-9 ]
[ 132973-03-6 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

4
[ 143-33-9 ]
[ 110223-15-9 ]
[ 75-07-0 ]
[ 85333-46-6 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.

5
[ 110223-15-9 ]
[ 78-95-5 ]
[ 85333-44-4 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.

6
[ 110223-15-9 ]
[ 87-13-8 ]
[ 132973-01-4 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

7
[ 110223-15-9 ]
[ 85333-46-6 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.

8
[ 110223-15-9 ]
[ 85333-45-5 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.

9
[ 110223-15-9 ]
[ 85333-49-9 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.
[2]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.

10
[ 110223-15-9 ]
[ 132973-07-0 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

11
[ 110223-15-9 ]
[ 132973-05-8 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

12
[ 84911-18-2 ]
[ 110223-15-9 ]
[ 850406-44-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; for 5h;Heating / reflux;	2-Bromo-3-oxo-butyric acid ethyl ester (15.6 g, 74.6 mmol) was added to a solution of <strong>[110223-15-9]2-amino-3-benzyloxypyrazine</strong> (Compound m in Scheme 1, 5 g, 24.9 mmol) in ethanol (20 mL). The reaction mixture was refluxed for 5 h. The reaction mixture was allowed to cool to r. t. and an off- white coloured solid precipitated out. The solid was collected and washed with ice-cold ethanol to give a white solid (1.08 g, 66%). 1H-NMR (DMSO-d6) No. 11.6 (br s, 1H), 7.97 (d, J5.7 Hz, 1H), 7.00 (t, J 5. 8-Hz, 1H), 4.35 (q, J 7.1 Hz, 2H), 2.52 (s, 3H), 1.34 (t, J 7.1 Hz, 3H); MS (ESI) 222.0 ([M+H])

References: [1]Patent: WO2005/34837,2005,A2 .Location in patent: Page/Page column 44-45.

13
[ 110223-15-9 ]
[ 2632-13-5 ]
[ 104462-06-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; for 5h;Heating / reflux;	2-Bromo-4'-methoxyacetophenone (1.64 g, 7.14 mmol) was added to a solution of 2- amino-3-benzyloxypyrazine (Compound m in scheme 1,1. 5 g, 6.80 mmol) in ethanol (10 mL). The reaction mixture was refluxed for 5 h. The reaction mixture was allowed to cool to r. t. and an off- white coloured solid precipitated out. The solid was collected and washed with ice-cold ethanol to give a white solid (1. 08 g, 66%). lH-NMR (CDC13) 6 11.4 (d, J4. 2 Hz, 1H), 8.23 (s, 1H), 7. 86 (t, J 2.9 Hz, 1H), 7. 83 (t, J2. 1 Hz, 1H), 7.52 (dd, J0. 7 & 5.5 Hz, 1H), 7.04 (t, J2. 9 Hz, 1H), 7.02 (t, J2. 0 Hz, 1H), 6.94 (t, J3.0 Hz, 1H), 3.79 (s, 3H) ; MS (ESI) 242.0 ([M+H]

References: [1]Patent: WO2005/34837,2005,A2 .Location in patent: Page/Page column 44.

14
[ 4544-43-8 ]
[ 110223-15-9 ]
[ 850406-45-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	In ethanol; for 5h;Heating / reflux;	2-Bromo-4,4, 4-trifluoro-3-oxo-butyric acid ethyl ester (2.61 g, 9.9 mmol) was added to a solution of <strong>[110223-15-9]2-amino-3-benzyloxypyrazine</strong> (Compound m in Scheme 1, 1 g, 5.0 mmol) in ethanol (10 mL). The reaction mixture was refluxed for 5 h. Upon cooling, a yellow precipitate formed from the reaction mixture. The solid was collected and washed with ice-cold ethanol to give a light yellow solid (0. 82g, 61%). 1H-NMR (CD3OD-d4) No. 8. 23 (d, J5. 9 Hz, 1H), 7.10 (d, J5. 9 Hz, 1H), 4.47 (q, J 7.1 Hz, 2H), 1.41 (t, J7. 1 Hz, 3H); MS (ES1) 276.0 ([M+H] +).

References: [1]Patent: WO2005/34837,2005,A2 .Location in patent: Page/Page column 45.

15
[ 110223-15-9 ]
4-amino-N-(3-(benzyloxy)pyrazin-2-yl)benzenesulfonamide [ No CAS ]

References: [1]MedChemComm,2014,vol. 5,p. 333 - 337.

16
[ 110223-15-9 ]
[ 1384274-27-4 ]

References: [1]MedChemComm,2014,vol. 5,p. 333 - 337.

17
[ 110223-15-9 ]
[ 121-60-8 ]
C₁₉H₁₈N₄O₄S [ No CAS ]

References: [1]MedChemComm,2014,vol. 5,p. 333 - 337.

18
[ 16744-98-2 ]
[ 110223-15-9 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(2-fluorophenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.43%	In tetrahydrofuran; for 8h;Reflux;	<strong>[110223-15-9]3-(benzyloxy)pyrazin-2-amine</strong> (100 mg, 0.5 mmol) and 2-fluoro isocyanate (0.67 mL, 0.60 mmol) in tetrahydrofuran (0.25 M) was dissolved in 8 hours during the heating under reflux thereby. After completion of the reaction, and concentrating the solvent under reduced pressure. The residue was washed with methanol and vacuum filter to give 122.6 mg of the desired compound in a yield of 69.43%.
69.4%	In tetrahydrofuran;Inert atmosphere; Schlenk technique; Reflux;	General procedure: 2-Amino-3-benzyloxypyridine or pyrazine derivative(2.5 mmol) was dissolved in dry THF (10 mL), isocyanate derivative(3.0 mmol) was added to the reaction mixture. The reaction wasrefluxed for 3-6 h. After cooling, the reaction mixture was evaporated and the residue was purified by solidification with cold methanol and filtered to give the target compounds.

References: [1]Patent: KR101481952,2015,B1 .Location in patent: Paragraph 0800; 0801.
[2]European Journal of Medicinal Chemistry,2018,vol. 144,p. 529 - 543.

19
[ 4411-25-0 ]
[ 110223-15-9 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(adamantane-1-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26.6%	With sodium hydride; In tetrahydrofuran; mineral oil; for 20h;Reflux;	3-(benzyloxy)pyridin-2-amine (100 mg, 0.50 mmol) and sodium hydride (60% in mineral oil, 22 mg, 0.55 mmol) was dissolved in tetrahydrofuran (0.25M) and then 1-adamantyl isocyanate (106 mg, 0.6 mmol) was added dropwise and heating at reflux for 20 hours. After the reaction was cooled to room temperature, water was added to terminate the reaction, and extracted with ethyl acetate, drying the extracted solution over sodium sulfate, it was filtered and concentrated under reduced pressure. By separation and purification of the residue by column chromatography (ethyl acetate / n-hexane = 1/2) to give the title compound 50 mg at a yield of 26.6%.

References: [1]Patent: KR101481952,2015,B1 .Location in patent: Paragraph 0892; 0893.

20
[ 1943-83-5 ]
[ 110223-15-9 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(2-chloroethyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.33%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 15h;Reflux;	3-(3-benzyloxy)pyrazin-2-amine (100 mg, 0.50 mmol) and 2-chloroethyl isocyanate (50 muL, 0.60 mmol), DIPEA (0.26 mL, 1.50 mmol) was dissolved in tetrahydrofuran (0.25 M ) and heated under reflux for 15 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate / n-hexane = 1/2) to give the title compound 109 mg at a yield of 71.33%.
71.3%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 18h;Inert atmosphere; Schlenk technique; Reflux;	General procedure: 2-Chloroethyl isocyanate (0.1 mL, 1.1 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.92 mmol) in dry THF (5 mL) in the presence of DIPEA (0.5 mL,2.75 mmol). The reaction mixture was refluxed for 18 h and evaporatedafter cooling. The residue was purified by flash columnchromatography (SiO2, EA/n-Hex 1/4).

References: [1]Patent: KR101481952,2015,B1 .Location in patent: Paragraph 0952; 0953.
[2]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

21
[ 110223-15-9 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(2-(4-methylpiperazin-1-yl)ethyl)urea [ No CAS ]

References: [1]Patent: KR101481952,2015,B1 .
[2]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

22
[ 110223-15-9 ]
[ 404-71-7 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(3-fluorophenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.8%	In tetrahydrofuran;Inert atmosphere; Schlenk technique; Reflux;	General procedure: 2-Amino-3-benzyloxypyridine or pyrazine derivative(2.5 mmol) was dissolved in dry THF (10 mL), isocyanate derivative(3.0 mmol) was added to the reaction mixture. The reaction wasrefluxed for 3-6 h. After cooling, the reaction mixture was evaporated and the residue was purified by solidification with cold methanol and filtered to give the target compounds.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 144,p. 529 - 543.

23
[ 4747-68-6 ]
[ 110223-15-9 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-cycloheptylurea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46.2%	With sodium hydride; In tetrahydrofuran; mineral oil; for 5h;Inert atmosphere; Schlenk technique; Reflux;	General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

24
[ 1611-57-0 ]
[ 110223-15-9 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(2,4,4-trimethylpentane-2-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.1%	With sodium hydride; In tetrahydrofuran; mineral oil;Inert atmosphere; Schlenk technique; Reflux;	General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

25
[ 110223-15-9 ]
[ 1609-86-5 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(tert-butyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16.3%	With sodium hydride; In tetrahydrofuran; mineral oil;Inert atmosphere; Schlenk technique; Reflux;	General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

26
[ 110223-15-9 ]
[ 103-71-9 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-phenylurea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.8%	In tetrahydrofuran; mineral oil;Inert atmosphere; Schlenk technique; Reflux;	General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

27
[ 110223-15-9 ]
[ 102-36-3 ]
1-(3-(benzyloxy)pyrazin-2-yl)-3-(3,4-dichlorophenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.1%	In tetrahydrofuran; mineral oil;Inert atmosphere; Schlenk technique; Reflux;	General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 268 - 278.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Nomenclature of Ethers • Petasis Reaction • Preparation of Amines • Preparation of Ethers • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 110223-15-9 ]

Aryls

A125872 [187973-44-0]

2-Amino-3-benzyloxy-5-bromopyrazine

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A113746 [24016-03-3]

2-Amino-3-benzyloxypyridine

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A119963 [1214900-01-2]

2-(Benzyloxy)pyridin-4-amine

Similarity: 0.59

A224285 [885952-26-1]

2-Benzyloxy-3-hydroxypyridine

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A180879 [635712-99-1]

6-(Benzyloxy)nicotinaldehyde

Similarity: 0.57

Ethers

A125872 [187973-44-0]

2-Amino-3-benzyloxy-5-bromopyrazine

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A119050 [89464-86-8]

2-Amino-3-ethoxypyrazine

Similarity: 0.75

A112847 [4774-10-1]

3-Methoxypyrazin-2-amine

Similarity: 0.71

A101427 [210993-11-6]

2-Hydrazinyl-3-methoxypyrazine

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A242676 [874-31-7]

2-Amino-5-chloro-3-methoxypyrazine

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Amines

A125872 [187973-44-0]

2-Amino-3-benzyloxy-5-bromopyrazine

Similarity: 0.85

A119050 [89464-86-8]

2-Amino-3-ethoxypyrazine

Similarity: 0.75

A112847 [4774-10-1]

3-Methoxypyrazin-2-amine

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A101427 [210993-11-6]

2-Hydrazinyl-3-methoxypyrazine

Similarity: 0.66

A242676 [874-31-7]

2-Amino-5-chloro-3-methoxypyrazine

Similarity: 0.65

Related Parent Nucleus of
[ 110223-15-9 ]

Pyrazines

A125872 [187973-44-0]

2-Amino-3-benzyloxy-5-bromopyrazine

Similarity: 0.85

A119050 [89464-86-8]

2-Amino-3-ethoxypyrazine

Similarity: 0.75

A112847 [4774-10-1]

3-Methoxypyrazin-2-amine

Similarity: 0.71

A101427 [210993-11-6]

2-Hydrazinyl-3-methoxypyrazine

Similarity: 0.66

A242676 [874-31-7]

2-Amino-5-chloro-3-methoxypyrazine

Similarity: 0.65

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P401
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Physical hazards
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H202	Explosive; severe projection hazard
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Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
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H311	Toxic in contact with skin
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H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 110223-15-9

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