19858-50-5|(2-(Methylthio)pyrimidin-5-yl)methanol| Ambeed

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Quality Control of [ 19858-50-5 ] Purity: 97% SDS Specification

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Product Details of [ 19858-50-5 ]

CAS No. :	19858-50-5
Formula :	C₆H₈N₂OS
M.W :	156.21
SMILES Code :	CSC1=NC=C(CO)C=N1
MDL No. :	MFCD11053756
InChI Key :	ZEIJWLQVULZDCE-UHFFFAOYSA-N
Pubchem ID :	22050485

Safety of [ 19858-50-5 ]

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

Computational Chemistry of [ 19858-50-5 ] 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	39.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.31 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.62
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	0.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.54
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	1.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.65

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.22
Solubility	9.38 mg/ml ; 0.0601 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.	-1.21
Solubility	9.53 mg/ml ; 0.061 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	-1.97
Solubility	1.69 mg/ml ; 0.0108 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.	-7.14 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)	1.32

Application In Synthesis of [ 19858-50-5 ]

* 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 [ 19858-50-5 ]

[ 19858-50-5 ] Synthesis Path-Downstream 1~22

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 0 - 20℃; for 2.0h;	General procedure: To a solution of ester in THF is added DIBAL-H dropwise at 0 °C. After stirring at room temperature for 2 hours, water, 15percent NaOH solution, water, and anhydrous sodium sulfate are added sequentiallly at 0 °C. The resulting slurry is stirred at room temperature for 1 hour and then filtered. The filter cake is washed with EA and the filtrate is concentrated.Following Procedure D using 13 (819 mg, 3.17 mmol), THF (5 mL), DIBAL- H (1.5 M in toluene, 8.4 mL, 12.6 mmol), then quench with water (0.50 mL), 15percent NaOH solution (0.50 mL), water (1.26 mL), and anhydrous sodium sulfate (5 g), and purify with silica gel column chromatography (EA:PE = 1 : 1) to give A17 as a white solid (610 mg, 89percent yield). (MS: [M+H]+ 217.0)

2
[ 73781-88-1 ]
[ 19858-50-5 ]
[ 1108737-66-1 ]

References: [1]Journal of Chemical Research,2007,p. 490 - 493.
[2]Journal of Chemical Research,2007,p. 490 - 493.

3
C₁₁H₁₄N₂O₄S [ No CAS ]
[ 19858-50-5 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8421 - 8439.

4
[ 19858-50-5 ]
[ 124-63-0 ]
C₇H₁₀N₂O₃S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8421 - 8439.

5
[ 19858-50-5 ]
[ 323591-23-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 16.0h;	To a mixture of 113 (1.02 g, 653 mrnoi) and PPh3 (3.4g, 131 mmol)in DCM (50 mL) is added carbon tetrabromide (4.3 g, 13.1 rnrnoi). After stirring at room temperature for 16 hours, the mixture is diluted with DCM, washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (EA:PE 1:20) to give 137 as a pale yellow oil (900 mg, 63percent). (MS: [M÷H] 2190)
	With dibromo sulfoxide; In dichloromethane; at 20℃; for 2.5h;	To a solution of the above compound (0.19 g, 1.2 mmol) in 8.5 mL CH2CI2 was added thionyl bromide (0.1 1 mL, 1.5 mmol). The reaction was stirred at room temperature for 2.5 h and quenched with saturated aqueous ammonium chloride. The layers were separated, and the organic portion was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to afford 5-(bromomethyl)-2-(methylsulfanyl)pyrimidine that gave a mass ion (ES+) of 221.1 (83/4Br) for M+H\\
	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 1.0h;	To the solution of <strong>[19858-50-5](2-(methylthio)pyrimidin-5-yl)methanol</strong> (0.88 g, 5.6 mmol) in DCM (20 ml) at 0°C was added triphenylphosphine (2.1 g, 7.9 mmol) and carbon tetrabromide(2.6 g, 7.9 mmol). The resulting solution was stirred at 0°C for 1 hour. The reaction mixture was purified on silica gel column using EtOAc/hexane as eluting solvents to give 5- (bromomethyl)-2-(methylthio)pyrimidine. LC/MS: (M+ 1 ): 218.90; 220.90.

References: [1]Patent: WO2017/176812,2017,A1 .Location in patent: Paragraph 0396.
[2]Patent: WO2011/84368,2011,A1 .Location in patent: Page/Page column 59.
[3]Patent: WO2015/171474,2015,A1 .Location in patent: Page/Page column 172; 173.

6
[ 19858-50-5 ]
[ 1314141-57-5 ]

References: [1]Patent: WO2011/84368,2011,A1 .

7
[ 38275-41-1 ]
[ 19858-50-5 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 14N-[(3/^,43/4-3-Hydroxytetrahydro-2H-pyran-4-yl]-4-[2-(methylsulfanyl)pyrimidin-5- yljmethyl } quinoline-2-carboxamideEthyl 4-(4,4,5,5-tetramethyl-l ,3i2-dioxaborolan-2-yl)quinoline-2-cai-boxylate (K4) was prepared as described in Example 11.To a solution of methyl 2-(methylsulfanyl)pyrimidine-5-carboxylate (Nl) (0.23 g, 1.2 mmol) in 20 mL THF at -78 °C was added disobutylaluminum hydride (3.2 mL, 1.0 M solution in toluene). The reaction mixture stirred for 40 min at -78 °C, and then additional disobutylaluminum hydride (5 eq.) was added dropwise. The reaction mixture was stirred for 2 h, and then quenched with concentrated acetic acid. The reaction mixture was warmed to room temperature and filtered to obtain a biphasic solution. The layers were separated, and the organics were dried over sodium sulfate, filtered, and concentrated to afford [2-(methylsuifanyl)pyrimidin-5-yl]methanol (N2) that gave a mass ion (ES+) of 157.1 for M+H+.
	With diisobutylaluminium hydride; In toluene; at -78 - 0℃; for 1.0h;	To the solution of methyl 2-(methylthio)pyrimidine-5-carboxylate (3.1 g, 17mmol) in toluene (100 ml) at -78°C was added DIBAL-H (42 ml, 42 mmol) dropwise. Theresulting solution was stirred at -78°C for 30 mm then warmed to 0°C for 30 mm. The reaction was quenched by addition of MeOH (2 mL), sat. Na2504 (50 ml), and iN NaOH (20 mL). The mixture was stirred at RT overnight. After filtration, the filtrate was extracted with EtOAc and DCM. The combined organic phase was dried over Na2504, concentrated and the residue waspurified on silica gel column using EtOAc/hexane as eluting solvents to give (2- (methylthio)pyrimidin-5 -yl)methanol. LC/MS: (M+ 1 ): 156.96.

References: [1]Patent: WO2011/84368,2011,A1 .Location in patent: Page/Page column 58-59.
[2]Patent: WO2015/171474,2015,A1 .Location in patent: Page/Page column 172.

8
[ 19858-50-5 ]
(S)-2-((S)-2-(2-(methylthio)pyrimidin-5-yl)-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)ethyl)pentanoic acid [ No CAS ]