698-29-3|4-Amino-2-methylpyrimidine-5-carbonitrile| Ambeed

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Quality Control of [ 698-29-3 ] Purity: 97% SDS Specification

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Product Details of [ 698-29-3 ]

CAS No. :	698-29-3
Formula :	C₆H₆N₄
M.W :	134.14
SMILES Code :	N#CC1=CN=C(C)N=C1N
MDL No. :	MFCD00084875
InChI Key :	YBPNIILOUYAGIF-UHFFFAOYSA-N
Pubchem ID :	69682

Safety of [ 698-29-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 698-29-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	36.12
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	75.59 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.21
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	0.53
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.25
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.	-0.88
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	0.57
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.45
Solubility	4.76 mg/ml ; 0.0355 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.	-1.69
Solubility	2.75 mg/ml ; 0.0205 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	-1.73
Solubility	2.47 mg/ml ; 0.0185 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	No
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.	-6.74 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)	1.76

Application In Synthesis of [ 698-29-3 ]

* 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.

Downstream synthetic route of [ 698-29-3 ]

[ 698-29-3 ] Synthesis Path-Downstream 1~35

1
[ 38875-74-0 ]
[ 698-29-3 ]

References: [1]Journal of the Chemical Society,1937,p. 367.
Journal of the Chemical Society,1938,p. 28.

2
[ 97-64-3 ]
[ 698-29-3 ]
<i>N</i>-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-lactamide [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 553.
Chem.Abstr.,1951,p. 5619.

3
[ 698-29-3 ]
[ 77287-34-4 ]
[ 118801-92-6 ]

References: [1]Journal Of Scientific and Industrial Research,1959,vol. 18B,p. 272,277.

4
[ 698-29-3 ]
[ 77287-34-4 ]
[ 1886-34-6 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 520,522,523.
Chem.Abstr.,1951,p. 5640.

5
[ 698-29-3 ]
[ 77287-34-4 ]
[ 108482-83-3 ]
[ 1886-34-6 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 520,522,523.
Chem.Abstr.,1951,p. 5640.

6
[ 698-29-3 ]
[ 113-00-8 ]
4,6-bis-(4-amino-2-methyl-pyrimidin-5-yl)-[1,3,5]triazin-2-ylamine [ No CAS ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 4922,4924.

7
[ 698-29-3 ]
[ 109-94-4 ]
[ 1886-34-6 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 520,522,523.
Chem.Abstr.,1951,p. 5640.

8
[ 698-29-3 ]
[ 109-94-4 ]
[ 108482-83-3 ]
[ 1886-34-6 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 520,522,523.
Chem.Abstr.,1951,p. 5640.

9
[ 698-29-3 ]
[ 73-68-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With formic acid; nickel; In water; for 0.25h;Reflux;	(0273) To a solution of the compound of Reference Example 22 (50.0 g, 373 mmol) in formic acid (150 mL) were added water (65 mL) and Raney nickel (50 g). The mixture was heated under reflux for 15 minutes, cooled to room temperature, and filtrated through Celite, and then 28% ammonia water (220 mL) was added thereto under ice cooling. The mixture was stirred under ice cooling for 1 hour, and the precipitate was collected by filtration. The filter cake was washed with water (30 mL) and chloroform (30 mL×2), and dried in vacuo. Furthermore, the filtrate was extracted with chloroform (200 mL) nine times, and the combined organic layer was concentrated. The resulting concentrated residue and the above-obtained filter cake were mixed, chloroform (70 mL) was added thereto, the mixture was stirred at room temperature for 30 minutes, hexane (210 mL) was added dropwise thereto over 10 minutes, and the mixture was stirred at room temperature for additional 1 hour. The precipitate was collected by filtration, washed with hexane/chloroform (3/1, 28 mL), and dried in vacuo to give the title compound (42.6 g, 83%). 1H-NMR (400 MHz, CDCl3) delta: 2.57 (3H, s), 5.98 (1H, brs), 8.15 (1H, brs), 8.57 (1H, s), 9.86 (1H, s).
83%	With formic acid; In water; for 0.25h;Reflux;	Compound of Reference Example 22 (50.0g, 373mmol) was added to the formic acid solution (150mL) and water (65mL) Raney nickel (50g). After heating to reflux for 15 min, cooled to room temperature, filtered through celite, under ice-cooling 28% aqueous ammonia (220 mL) was added, after stirring for 1 hour under ice-cooling, the precipitate was collected by filtration. The filtrate quality goods and washed with water (30 mL) and chloroform (30 mL × 2 times) followed by drying under reduced pressure. Further, the filtrate was extracted 9 times with chloroform (200 mL), the organic layer was concentrated. The combined quality goods braze obtained this concentrated residue before, chloroform (70 mL) was added, after stirring for 30 minutes at room temperature, hexane (210 mL) was added dropwise over 10 minutes, further stirred at room temperature for 1 hour. Thereafter, the precipitate was collected by filtration, washed with hexane / chloroform (3 / 1,28mL), the title compound was dried under reduced pressure (42.6g, 83%) was obtained.
70%	With sulfuric acid; palladium 10% on activated carbon; hydrogen; In water; at 20℃; for 16h;	To a solution of 51 (700 mg, 5.2 rnrnoi) in water and H2S04 is added Pd/C (10 wt. %, 543 mg). After stirring at room temperature under hydrogen for 16 hours, the mixture is filtered through a. pad of? Celite and washed with water. The filtrate is treated with ammonium hydroxide, and the solid is collected by filtration and dried to give 52 (500 mg, 70%). (MS: [M±HI 1381)

58.5%		4-Amino-2-methylpyrimidine-5-carbonitrile (500 mg, 3.73 mmol) and 10% palladium on carbon (40.8 mg, 38.3 mumol) were combined in water (4 mL) and sulfuric acid (800 muL). The mixture was hydrogenated at room temperature and 30-50 psi for 75 minutes. The reaction mixture was filtered through Celite and washed with water. The filtrate was combined with the washes and treated with concentrated ammonium hydroxide. Solid precipitated out of solution, with heat given off. The mixture was chilled prior to collecting the solid by filtration. The filtered solid was washed with water and then dried under house vacuum to give 4-amino-2-methylpyrimidine-5-carbaldehyde. (Yield 299.2 mg, 2.18 mmol, 58.5%).
	With formic acid; at 80℃; for 4h;	A solution of <strong>[698-29-3]4-amino-2-methylpyrimidine-5-carbonitrile</strong> 1a (3.04g, 30mmol) and raney nickel (3.0g) in formic acid (20mL) was stirred at 80C for 4h. After this, the reaction mixture was filtered and washed with 10mL formic acid. The filtrate and washings were collected together and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and eluted with ethyl acetate/petroleum ether (1:1, v/v) to give white solid 2a, which was used directly for the next step. Under this same condition, the intermediate compounds 2a and 2c were also prepared.

References: [1]Patent: US2016/122319,2016,A1 .Location in patent: Paragraph 0272-0273.
[2]Patent: JP2016/108326,2016,A .Location in patent: Paragraph 0208; 0209.
[3]Patent: WO2017/176812,2017,A1 .Location in patent: Paragraph 0281.
[4]Patent: US2012/184542,2012,A1 .Location in patent: Page/Page column 58; 59.
[5]Bulletin de la Societe Chimique de France,1938,vol. <5> 5,p. 1539,1542.
[6]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1952,vol. 72,p. 630.
Chem.Abstr.,1953,p. 2177.
[7]Journal of Medicinal Chemistry,1981,vol. 24,p. 382 - 389.
[8]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ni: MVol.C2, 7.12, page 724 - 733.
[9]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5652 - 5661.

10
[ 698-29-3 ]
[ 73-67-6 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1952,vol. 72,p. 630.
Chem.Abstr.,1953,p. 2177.
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 2963 - 2966.

11
[ 698-29-3 ]
[ 95-02-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With ammonia; hydrogen; In methanol; at 60℃; under 30003 Torr; for 24h;Autoclave;	[0267j In an autoclave the mixture of <strong>[698-29-3]4-amino-2-methylpyrimidine-5-carbonitrile</strong> (16 g, 119 mmol), modified Raney nickel (wet weight 15 g), and saturated methanol solution of ammonia (200 mL) was heated to 60 C and stirred for 24 hrs at this temperature under 4 MPa of hydrogen pressure. The resulting reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (CH2C12/MeOH = 30/ii0/i) to afford 14.8 g of 5 -(aminomethyl)-2-methylpyrimidin-4-amine (90 %).

References: [1]Organic Process Research and Development,2012,vol. 16,p. 57 - 60.
[2]Patent: WO2013/177536,2013,A2 .Location in patent: Paragraph 0267.
[3]Chemische Berichte,1953,vol. 86,p. 1404,1406.
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1942,vol. 62,p. 417,443;dtsch.Ref.S.122,125.
    Chem.Abstr.,1951,p. 4724.
[5],1953,vol. 21,p. 66.
    Chem.Abstr.,1953,p. 6796.
[6]Takamine Kenkyusho Nenpo,1956,vol. 8,p. 36,38.
    Chem.Abstr.,1958,p. 395.
[7]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 62,64.
    Chem.Abstr.,1950,p. 5368.
[8]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1936,vol. 242,p. 89,94.
[9]Patent: US2449036,1946, .
[10]Patent: CH244837,1945, .

12
[ 698-29-3 ]
[ 7389-14-2 ]

References: [1]Chemische Berichte,1958,vol. 91,p. 1834,1839.
[2]Journal Of Scientific and Industrial Research,1958,vol. 17 B,p. 63,68.

13
[ 698-29-3 ]
[ 82302-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydrogen sulfide; triethylamine; In N-methyl-acetamide;	EXAMPLE 8 4-Amino-2-methyl-5-pyrimidinecarbothioamide Hydrogen sulfide is passed through a mixture of 4-amino-2-methyl-5-pyrimidinecarbonitrile (6.707 g., 0.050 m.), triethylamine (7.0 ml., 0.050 m.), dimethylformamide (25 ml.) and pyridine (100 ml.) with stirring for 3 hours at ambient temperature. The mixture is poured into ice water (500 ml.) and the cream-colored solid which separates is collected by filtration, washed with water, dried at 110 C./0.1 mm. The yield of product melting at 260 C. dec. (uncorr.) is 7.663 g. (91.1%). This material is recrystallized from dimethylformamide-water (Darco G-60) affording colorless crystals melting at 264 C. dec. (uncorr.) in a yield of 5.110 g. (60.8%). Analysis for: C6 H8 N4 S; Calculated: C, 42.83; H, 4.79; N, 33.32; S, 19.06; Found: C, 42.79; H, 4.83; N, 33.34; S, 19.19.

References: [1]Journal Of Scientific and Industrial Research,1959,vol. 18B,p. 272,277.
[2]Patent: US4323681,1982,A .

14
[ 698-29-3 ]
[ 769-52-8 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 2818.
[2]Journal of the American Chemical Society,1940,vol. 62,p. 2818.
[3]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 626 - 632.

15
[ 698-29-3 ]
[ 108482-83-3 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 62,64.
Chem.Abstr.,1950,p. 5368.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 62,64.
Chem.Abstr.,1950,p. 5368.

16
[ 698-29-3 ]
[ 87647-08-3 ]

References: [1]Journal of the American Chemical Society,1944,vol. 66,p. 876,877.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 62,64.
    Chem.Abstr.,1950,p. 5368.
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 62,64.
    Chem.Abstr.,1950,p. 5368.
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1953,vol. 73,p. 977,979,981.
    Chem.Abstr.,1954,p. 11426.

17
[ 7389-14-2 ]
[ 698-29-3 ]

References: [1]Journal of the Chemical Society,1937,p. 367.
Journal of the Chemical Society,1938,p. 28.

18
[ 874495-29-1 ]
[ 698-29-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1955,vol. 20,p. 52,56.

19
[ 76574-37-3 ]
[ 698-29-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1955,vol. 20,p. 52,56.

20
[ 64-17-5 ]
[ 2208-07-3 ]
[ 672-25-3 ]
[ 698-29-3 ]

References: [1]Patent: DE667990,1936, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 25,p. 432,434.

21
[ 3613-29-4 ]
[ 672-25-3 ]
[ 698-29-3 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1947,vol. 67,p. 161,164.
Chem.Abstr.,1951,p. 9545.

22
[ 64-18-6 ]
[ 698-29-3 ]
[ 73-68-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2963 - 2966.

23
[ 124-42-5 ]
[ 123-06-8 ]
[ 698-29-3 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of sodium ethoxide (1.15g, 50mmol), and acetamidine hydrochloride (4.7g, 50mmol) in ethanol solution (60mL) was stirred at room temperature for 1h. After this, the reaction mixture was filtered out affording filtrate. Then 2-(ethoxymethylene)malononitrile (6.1g, 50mmol) was added to the filtrate, and the mixture was stirred at room temperature for 3h. After this, the reaction mixture was filtered and washed with 10mL ethanol and dried to give the desired compound 4-amino-2-methylpyrimidine-5-carbonitrile 1a, which was used directly for the next step. Under the same condition, the intermediate compounds 1b and 1c were also prepared.

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2963 - 2966.
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 382 - 389.
[3]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5652 - 5661.

24
[ 698-29-3 ]
4-amino-5-(S)-hydroxydeuteriomethyl-2-methylpyrimidine [ No CAS ]