39268-74-1|5-Ethoxypyrimidin-2-amine| Ambeed

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Quality Control of [ 39268-74-1 ] Purity: 97% SDS Specification

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Product Details of [ 39268-74-1 ]

CAS No. :	39268-74-1
Formula :	C₆H₉N₃O
M.W :	139.16
SMILES Code :	CCOC1=CN=C(N)N=C1
MDL No. :	MFCD00223638
InChI Key :	NGWGYIGTWBAKAN-UHFFFAOYSA-N
Pubchem ID :	45080359

Safety of [ 39268-74-1 ]

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

Computational Chemistry of [ 39268-74-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	37.74
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.	1.57
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.	0.47
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.	-0.52
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	0.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.43

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.13
Solubility	10.2 mg/ml ; 0.0734 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.	-1.03
Solubility	13.0 mg/ml ; 0.0933 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	-1.8
Solubility	2.22 mg/ml ; 0.0159 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.	-7.01 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)	1.79

Application In Synthesis of [ 39268-74-1 ]

* 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 [ 39268-74-1 ]

[ 39268-74-1 ] Synthesis Path-Downstream 1~11

2
[ 39268-74-1 ]
[ 1312938-69-4 ]

References: [1]Patent: US2012/225896,2012,A1 .

3
[ 39268-74-1 ]
[ 1312938-93-4 ]

References: [1]Patent: US2012/225896,2012,A1 .

4
[ 39268-74-1 ]
[ 1312938-94-5 ]

References: [1]Patent: US2012/225896,2012,A1 .

5
[ 39268-74-1 ]
[ 1312938-95-6 ]

References: [1]Patent: US2012/225896,2012,A1 .

6
[ 674-82-8 ]
[ 39268-74-1 ]
[ 1312938-92-3 ]

Yield	Reaction Conditions	Operation in experiment
38%	With triethylamine; In ethyl acetate; toluene; at 85℃; for 24.5h;Reflux;	Example 11 Production of 3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-4-butyl-1-(5-ethoxypyrimidin-2-yl)-6-methylpyridin-2(1H)-one Process 1: Diketene (2.8 mL, 36 mmol) and triethylamine (2 mL, 14 mmol) were added to a toluene (30 mL) solution of <strong>[39268-74-1]2-amino-5-ethoxypyrimidine</strong> (1.4 g, 10 mmol) and stirred for 24 hours at 85 C. The solvent was distilled off and the mixture was added ethyl acetate (10 mL) and heated under reflux for 30 min. After cooling to room temperature, the solution was filtered to obtain 3-acetyl-1-(5-ethoxypyrimidin-2-yl)-4-hydroxy-6-methylpyridin-2(1H)-one (1.10 g, 38%) as a black solid. 1H-NMR (CDCl3) delta: 1.51 (3H, t, J=7 Hz), 1.99 (3H, s), 2.68 (3H, s), 4.22 (2H, t, J=7 Hz), 5.93 (1H, s), 8.52 (2H, s).

References: [1]Patent: US2012/225896,2012,A1 .Location in patent: Page/Page column 17.

7
[ 39268-74-1 ]
[ 1312938-71-8 ]

References: [1]Patent: US2012/225896,2012,A1 .

8
[ 39268-74-1 ]
[ 1312939-08-4 ]

References: [1]Patent: US2012/225896,2012,A1 .

9
[ 39268-74-1 ]
[ 1312938-96-7 ]

References: [1]Patent: US2012/225896,2012,A1 .

10
[ 1400997-38-7 ]
[ 39268-74-1 ]
[ 1400997-42-3 ]

Yield	Reaction Conditions	Operation in experiment
18%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere;	EXAMPLE 100(RS)-(5-Ethoxy-pyrimidin-2-yl)-(2-fluoro-4-morpholin-2-yl-phenyl)-aminea) (RS)-2-[4-(5-Ethoxy-pyrimidin-2-ylamino)-3-fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl esterTo a 10 ml glass vial was added (RS)-2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (70 mg, Example 96(e)) and <strong>[39268-74-1]5-ethoxy-2-pyrimidinamine</strong> (40.6 mg, CAS 39268-74-1) in dioxane (2 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (13.6 mg), tris(dibenzylideneacetone)dipalladium(0) (7.12 mg) and sodium tert-butoxide (21.0 mg) were then added. The vial was capped and heated at 120 C. for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in hexanes) to afford (RS)-2-[4-(5-ethoxy-pyrimidin-2-ylamino)-3-fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (15 mg, 18%) as a yellow gum. MS (ISP): 441.4 ([M+Na]+), 419.3 ([M+H]+).
18%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere; capped vial;	To a 10 ml glass vial was added (RS)-2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (70 mg, Example 96(e)) and <strong>[39268-74-1]5-ethoxy-2-pyrimidinamine</strong> (40.6 mg, CAS 39268-74-1) in dioxane (2 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert- butylphosphino-2',4',6'-triisopropylbiphenyl (13.6 mg), tris(dibenzylideneacetone)dipalladium(0) (7.12 mg) and sodium tert-butoxide (21.0 mg) were then added. The vial was capped and heated at 120 C for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in hexanes) to afford (RS)-2-[4-(5-ethoxy-pyrimidin-2-ylamino)-3- fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (15 mg, 18%) as a yellow gum. MS (ISP): 441.4 ([M+Na]+), 419.3 ([M+H]+).

References: [1]Patent: US2012/245172,2012,A1 .Location in patent: Page/Page column 52.
[2]Patent: WO2012/126922,2012,A1 .Location in patent: Page/Page column 92; 93.

11
methyl (Z)-2-[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-isobutylamide-2-hexenoate [ No CAS ]
[ 39268-74-1 ]
[ 1400690-97-2 ]

Yield	Reaction Conditions	Operation in experiment
58%		Process 4: Under argon atmosphere, trimethylaluminum (2 mol/L hexane solution, 0.39 mL, 0.78 mmol) was added to 1,2-dichloroethane (5 mL) solution of <strong>[39268-74-1]2-amino-5-ethoxypyrimidine</strong> (108 mg, 0.78 mmol) at room temperature and stirred for 70 minutes at room temperature. 1,2-dichloroethane solution (2 mL) of methyl (Z)-2-[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-isobutylami de-2-hexenoate (158 mg, 0.39 mmol) was added dropwise thereto at room temperature and refluxed under heating for 3 hours. The reaction mixture was added an aqueous solution of ammonium chloride and chloroform, and filtered through a pad of celite. The organic layer in the filtrate was separated and the aqueous layer was extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residues were subjected to silica gel column chromatography (Flash12M manufactured by Biotage) (chloroform/methanol = 40 : 1) to give 2-{5-[1-(5-ethoxypyrimidin-2-yl)-2-isopropyl-6-oxo-4-propy 1-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitril e (111 mg, 58%) as yellow oil. 1H-NMR(CDCl3, 400 MHz)delta: 0.97(3H, t, J = 7.4 Hz), 1.17(6H, d, J = 6.6 Hz), 1.49(3H, t, J=6.9Hz), 1.66-1.77(2H, m), 2.19-2.32(1H, m), 2.60-2.70(2H, m), 3.93(2H, s), 4.10(2H, q, J = 7.1 Hz), 7.45(1H, td, J = 7.7, 1.1 Hz), 7.60 - 7.67(2H, m), 7.73 - 7.80(3H, m), 8.49 (2H, s), 8.67(1H, d, J = 1.3 Hz).

References: [1]Patent: EP2687523,2014,A1 .Location in patent: Paragraph 0189.

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 Ethers • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 39268-74-1 ]

Ethers

A163780 [13418-77-4]

2-Amino-5-methoxypyrimidine

Similarity: 0.96

A111941 [1006599-54-7]

5-(2-(Methylthio)ethoxy)pyrimidin-2-amine

Similarity: 0.87

A418376 [1355074-03-1]

5-Ethoxypyrimidin-4-amine

Similarity: 0.72

A205532 [22536-65-8]

2-Chloro-5-methoxypyrimidine

Similarity: 0.70

A120252 [695-86-3]

5-Methoxypyrimidin-4-amine

Similarity: 0.68

Amines

A163780 [13418-77-4]

2-Amino-5-methoxypyrimidine

Similarity: 0.96

A110115 [143489-45-6]

2-Aminopyrimidin-5-ol

Similarity: 0.87

A111941 [1006599-54-7]

5-(2-(Methylthio)ethoxy)pyrimidin-2-amine

Similarity: 0.87

A418376 [1355074-03-1]

5-Ethoxypyrimidin-4-amine

Similarity: 0.72

A230172 [52601-89-5]

4-Aminopyrimidin-5-ol

Similarity: 0.71

Related Parent Nucleus of
[ 39268-74-1 ]

Pyrimidines

A163780 [13418-77-4]

2-Amino-5-methoxypyrimidine

Similarity: 0.96

A110115 [143489-45-6]

2-Aminopyrimidin-5-ol

Similarity: 0.87

A111941 [1006599-54-7]

5-(2-(Methylthio)ethoxy)pyrimidin-2-amine

Similarity: 0.87

A529026 [26456-59-7]

Pyrimidin-5-ol

Similarity: 0.74

A418376 [1355074-03-1]

5-Ethoxypyrimidin-4-amine

Similarity: 0.72

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H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
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
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
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.: 39268-74-1

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