13134-38-8|3,6-Dimethylpyrazin-2-amine| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 13134-38-8 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 13134-38-8 ]

CAS No. :	13134-38-8
Formula :	C₆H₉N₃
M.W :	123.16
SMILES Code :	NC1=NC(C)=CN=C1C
MDL No. :	MFCD18917551
InChI Key :	HYZYHVUIWRRMEZ-UHFFFAOYSA-N
Pubchem ID :	13261500

Safety of [ 13134-38-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 13134-38-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	36.37
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	51.8 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.27
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	0.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.68
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.	-0.34
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	1.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.57

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.22
Solubility	7.48 mg/ml ; 0.0607 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.84
Solubility	18.0 mg/ml ; 0.146 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.02
Solubility	1.17 mg/ml ; 0.00951 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	No
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.	-6.92 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	1.0
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)	1.82

Application In Synthesis of [ 13134-38-8 ]

* 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 [ 13134-38-8 ]

[ 13134-38-8 ] Synthesis Path-Downstream 1~36

1
[ 123-32-0 ]
[ 13134-38-8 ]

Yield	Reaction Conditions	Operation in experiment
10%	With sodium amide; In N,N-dimethyl-aniline; at 170℃; for 1h;	(b) 3,6-Dimethylpyrazin-2-amine A mixture of 2,5-dimethylpyrazine (14 g, 0.13 mol) in N,N-dimethylaniline (50 mL) was heated to 170 C. and NaNH2 (22 g, 0.56 mol) was added in portions. The reaction mixture was stirred at 170 C. for 1 h, and the solvent was removed. The product was purified by silica gel column chromatography to give 3,6-dimethylpyrazin-2-amine as a brown solid (1.6 g, yield 10%). ESI MS: m/z 124 [M+1]+.
	With sodium amide; N,N-dimethyl-aniline; at 170℃;	(b) 3,6-Dimethylpyrazin-2-amine[00426] A mixture of 2,5-dimethylpyrazine (14 g, 0.13 mol) in N,N-dimethylaniline (50 mL) was heated to 170 C and NaNH2 (22 g, 0.56 mol) was added in portions. The reaction mixture was stirred at 170 C for 1 h, and the solvent was removed. The product was purified by column chromatography to give 3,6-dimethylpyrazin-2-amine as a brown solid (1.6 g). MS (ESI): m/z 124[M+H]+.

References: [1]Patent: US2012/178748,2012,A1 .Location in patent: Page/Page column 41.
[2]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1930,vol. 62,p. 1189,1193.
Chemisches Zentralblatt,1930,vol. 101,p. 3771.
[3]Journal of the American Chemical Society,1941,vol. 63,p. 1929.
[4]Patent: WO2011/150156,2011,A2 .Location in patent: Page/Page column 122.

2
[ 13134-38-8 ]
[ 98-88-4 ]
[ 10212-66-5 ]

References: [1]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1930,vol. 62,p. 1189,1193.
Chemisches Zentralblatt,1930,vol. 101,p. 3771.

3
[ 13134-38-8 ]
[ 123-62-6 ]
<i>N</i>-(3,6-dimethyl-pyrazin-2-yl)-propionamide [ No CAS ]

References: [1]Journal of the Chemical Society,1948,p. 1855,1859.
Journal of the Chemical Society,1949,p. 300.

4
[ 13134-38-8 ]
[ 103-80-0 ]
phenyl-acetic acid-(3,6-dimethyl-pyrazin-2-ylamide) [ No CAS ]

References: [1]Journal of the Chemical Society,1949,p. 300.

5
[ 13134-38-8 ]
[ 121-60-8 ]
[ 873377-13-0 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 1929.

6
[ 13134-38-8 ]
[ 91416-91-0 ]

References: [1]Heterocycles,1984,vol. 22,p. 1195 - 1210.

7
[ 83505-98-0 ]
[ 13134-38-8 ]

References: [1]Synthesis,1994,p. 931 - 934.

9
[ 95-89-6 ]
[ 13134-38-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With ammonia;copper; In water; at 150℃; for 48h;Autoclave;	a. 3,6-Dimethylpyrazin-2-amine A 100 mL autoclave vessel was charged with 3-chloro-2,5-dimethylpyrazine (25.0 g, 176 mmol), NH3 (aq. 25-28% w/w, 80 mL) and Cu powder (1.69 g, 26.4 mmol) and the autoclave vessel was sealed. The resulting mixture was heated to 150 C. and stirred vigorously for 48 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with brine (100 mL) and extracted with EtOAc (4*100 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was washed with PE to render the title compound as a light yellow solid (17.6 g, yield 81%). ESI MS: m/z 124 [M+H]+.
73%	With ammonium hydroxide; copper; at 150℃; for 22h;Sealed tube;	In a pressure tube were placed 4 mL of 25% ammonia solution, 64 mg of powdered copper and 1.0 g (6.66 mmol) of 3-chloro-2,5-dimethylpyrazine. The whole was heated to 150 C for 18 hours. Further 1 mL of 25% ammonia solution was added and heating was continued for further 4 hours. The mixture was filtered through silica gel layer, washed with 10 mL of water and 10 mL of ethyl acetate. The filtrate was extracted with ethyl acetate (5 x 10 mL). Organic phase was dried over sodium sulphate and concentrated. Resulted solid was triturated with heptane and filtered-off (first crop). Second crop of the product crystallized from the filtrate. Combined solids were dried under reduced pressure to obtain 0.60 g of 2-amino-3,6-dimethyl- pyrazine as a solid (yield 73%). MR (300 MHz, DMSO-d6): delta 7.45 (s, 1H), 6.01 (s, broad, 2H), 2.22 (s, 3H), 2.10 (s, 3H).
109 mg	With ammonia; In water; at 165℃; for 23h;Microwave irradiation;	Intermediate 18: 3,6-d imethyllyrazin-2-amineAmmonia in water (3 mL, 48.5 mmol) was added to 3-chloro-2,5-dimethylpyrazine (0.121 mL, 1 mmol) and the mixture heated by microwaves to 165 C for 7 hours. Following LCMS analysis, the reaction was then reheated to 165 C for a further 16 hours, by microwaves. After cooling, thesolvent was removed under a stream of nitrogen and the crude redissolved in dichloromethane (20mL). Water (25 mL) was added and the mixture basified to pHl4 using sodium hydroxide solution(18 N). The organic layer was removed and the aqueous layer extracted with dichloromethane (5 x25 mL). The organic phases were combined and dried using a hydrophobic frit, then evaporated invacuoto give the title product (109 mg). This was used directly in the next step with no furtherpurification. LCMS (2 mm, high pH) Rt 0.47 mi m/z (ESj 124 (M+H).1H NMR (400 MHz, CHLOROFORM-o) O ppm 7.73 (5, 1 H), 4.42 (br. s., 2 H), 2.37 (5, 3 H), 2.35 (5, 3H).

109 mg

With ammonium hydroxide; at 165℃; for 23h;Microwave irradiation;

Ammonia in water (3 mL, 48.5 mmol) was added to 3-chloro-2,5-dimethylpyrazine (0.121 mL, 1 mmol) and the mixture heated by microwaves to 165 C. for 7 hours. Following LCMS analysis, the reaction was then reheated to 165 C. for a further 16 hours, by microwaves. After cooling, the solvent was removed under a stream of nitrogen and the crude redissolved in dichloromethane (20 mL). Water (25 mL) was added and the mixture basified to pH14 using sodium hydroxide solution (18 N). The organic layer was removed and the aqueous layer extracted with dichloromethane (5×25 mL). The organic phases were combined and dried using a hydrophobic frit, then evaporated in vacuo to give the title product (109 mg). This was used directly in the next step with no further purification. LCMS (2 min, high pH) Rt 0.47 min, m/z (ES+) 124 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.73 (s, 1H), 4.42 (br. s., 2H), 2.37 (s, 3H), 2.35 (s, 3H).

References: [1]Patent: US2012/178748,2012,A1 .Location in patent: Page/Page column 37.
[2]Patent: WO2015/177688,2015,A1 .Location in patent: Page/Page column 20.
[3]Synthesis,1994,p. 931 - 934.
[4]Patent: WO2013/160419,2013,A1 .Location in patent: Page/Page column 33.
[5]Patent: US2015/65507,2015,A1 .Location in patent: Paragraph 0169; 0170.

10
[ 13134-38-8 ]
[ 5433-89-6 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 1929.

11
tin(IV) chloride dihydrate [ No CAS ]
[ 83505-98-0 ]
[ 13134-38-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	With hydrogenchloride; In methanol; ethyl acetate;	Step 2: 2-Amino-3,6-dimethylpyrazine. To a stirred solution of 3-azido-2,5-dimethyl pyrazine (100 mg; 0.66 mmol) in methanol (800 muL) was added 12N HCl (100 muL) and tin chloride dihydrate (149 mg; 0.66 mmol). The reaction was heated to 60 C. and stirred for 12 hours. The reaction was cooled to room temperature, diluted with 50 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1*50 mL), brine (50 mL), then dried (MgSO4), and filtered. The material was purified using a biotage 12i cartridge eluding with ethyl acetate to yield an off white solid (38% yield).

References: [1]Patent: US2003/69284,2003,A1 .

12
[ 13134-38-8 ]
[ 36016-40-7 ]
[ 1351515-90-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	In dichloromethane; at 0 - 20℃; for 3h;	(c) 1-Amino-3,6-dimethylpyrazin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate A mixture of <strong>[13134-38-8]3,6-dimethylpyrazin-2-amine</strong> (1.23 g, 10 mmol) in DCM (20 mL) was cooled to 0 C. and a solution of O-(mesitylsulfonyl)hydroxylamine (4.3 g, 20 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature for 3 h and filtered. The solid collected was washed with DCM (50 mL) to give 1-amino-3,6-dimethylpyrazin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate as a brown solid (2.0 g, yield 59%). ESI MS: m/z 139 [M-199]+.
	In dichloromethane; at 0 - 20℃;	(c) l-Amino-3,6-dimethylpyrazin-2(lH)-iminium 2,4,6- trimethylbenzenesulfonate[00427] A mixture of <strong>[13134-38-8]3,6-dimethylpyrazin-2-amine</strong> (1.23 g, 10 mmol) in DCM (20 mL) was cooled to 0 C and a solution of 0-(mesitylsulfonyl)hydroxylamine (4.3 g, 20 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature, stirred for 3 h and then filtered. The solid collected was washed with DCM (50 mL) to give l -amino-3,6- dimethylpyrazin-2(lH)-iminium 2,4,6-trimethylbenzenesulfonate as a brown solid (2.0 g). MS (ESI): m/z 139[M-199]+.

References: [1]Patent: US2012/178748,2012,A1 .Location in patent: Page/Page column 41.
[2]Patent: WO2011/150156,2011,A2 .Location in patent: Page/Page column 122.

13
[ 13134-38-8 ]
[ 1201687-91-3 ]

References: [1]Patent: WO2011/150156,2011,A2 .
[2]Patent: US2012/178748,2012,A1 .

14
[ 13134-38-8 ]
[ 1201689-16-8 ]