211244-81-4|2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one| Ambeed

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Quality Control of [ 211244-81-4 ] Purity: 98% SDS Specification

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Product Details of [ 211244-81-4 ]

CAS No. :	211244-81-4
Formula :	C₈H₇N₃OS
M.W :	193.23
SMILES Code :	O=C1C=CC2=CN=C(SC)N=C2N1
MDL No. :	MFCD03084167
InChI Key :	WPUAPGRZGJOIBX-UHFFFAOYSA-N
Pubchem ID :	1234763

Safety of [ 211244-81-4 ]

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

Computational Chemistry of [ 211244-81-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	10
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	51.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	83.94 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.68
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	0.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.04
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.	0.95
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	2.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.31

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.04
Solubility	1.77 mg/ml ; 0.00914 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.	-2.13
Solubility	1.42 mg/ml ; 0.00735 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	-3.36
Solubility	0.0836 mg/ml ; 0.000433 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	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.	-6.92 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)	1.76

Application In Synthesis of [ 211244-81-4 ]

* 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 [ 211244-81-4 ]

[ 211244-81-4 ] Synthesis Path-Downstream 1~35

1
[ 75-30-9 ]
[ 211244-81-4 ]
[ 211244-94-9 ]

Yield	Reaction Conditions	Operation in experiment
140 mg (69%)	With NaH; In N-methyl-acetamide; ethyl acetate; mineral oil;	Example 33 8-Isopropyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> To a suspension of NaH (48 mg of a 60% suspension of NaH in mineral oil) in 6 mL of dimethylformamide was added <strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (158 mg, 0.82 mmol). The reaction mixture was heated to 50 C. resulting in a yellow solution. The solution was cooled slightly and 2-iodopropane (120 muL, 1.20 mmol) was added. The reaction was heated at 50 C. for 30 minutes then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluding with a gradient of 1:3 ethyl acetate:hexane to all ethyl acetate, to provide 140 mg (69%) of 8-isopropyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong>, mp 101-102 C. Analysis calculated for C11H13N3OS: C, 56.15; H, 5.57; N, 17.86. Found: C, 56.07; H, 5.59; N, 17.78.

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.
[2]Patent: US2004/224958,2004,A1 .

2
[ 54555-84-9 ]
[ 211244-81-4 ]
[ 1028271-73-9 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

3
[ 542-69-8 ]
[ 211244-81-4 ]
[ 352359-88-7 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

4
[ 513-48-4 ]
[ 211244-81-4 ]
[ 1028285-98-4 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

5
[ 513-38-2 ]
[ 211244-81-4 ]
[ 1026150-37-7 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

6
[ 1809-05-8 ]
[ 211244-81-4 ]
[ 352359-84-3 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

7
[ 554-10-9 ]
[ 211244-81-4 ]
[ 1026029-19-5 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

8
[ 2404-36-6 ]
[ 211244-81-4 ]
[ 211246-07-0 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

9
[ 19451-11-7 ]
[ 211244-81-4 ]
[ 211245-81-7 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

10
[ 1556-18-9 ]
[ 211244-81-4 ]
[ 211245-66-8 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

11
[ 626-62-0 ]
[ 211244-81-4 ]
[ 211245-79-3 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

12
[ 120497-57-6 ]
[ 211244-81-4 ]
8-bicyclo[2.2.1]hept-2-yl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

13
[ 75-03-6 ]
[ 211244-81-4 ]
[ 211244-82-5 ]

Yield	Reaction Conditions	Operation in experiment
192 mg (64%)	With NaH; In N-methyl-acetamide; mineral oil;	Example 21 8-Ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> To a suspension of NaH (80 mg of a 60% suspension of NaH in mineral oil) in 10 mL of dimethylformamide was added <strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (262 mg, 1.35 mmol). The reaction mixture was heated to 50 C. resulting in a brown solution. The solution was cooled slightly and iodoethane (150 muL, 1.88 mmol) was added. The reaction was heated at 50 C. for 10 minutes, then cooled to room temperature and partitioned between cold water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluding with 1:1 ethyl acetate:hexane to all ethyl acetate, to provide 192 mg (64%) of 8-ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong>, mp 104-106 C. Analysis calculated for C10H11N3OS: C, 54.28; H, 5.01; N, 18.99. Found: C, 54.28; H. 5.03; N, 19.06.
192 mg (64%)	With NaH; In N-methyl-acetamide; mineral oil;	Example 21 8-Ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> To a suspension of NaH (80 mg of a 60% suspension of NaH in mineral oil) in 10 mL of dimethylformamide was added <strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (262 mg, 1.35 mmol). The reaction mixture was heated to 50 C. resulting in a brown solution. The solution was cooled slightly and iodoethane (150 mL, 1.88 mmol) was added. The reaction was heated at 50 C. for 10 minutes, then cooled to room temperature and partitioned between cold water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluding with 1:1 ethyl acetate:hexane to all ethyl acetate, to provide 192 mg (64%) of 8-ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong>, mp 104-106 C. Analysis calculated for C10H11N3OS: C, 54.28; H, 5.01; N, 18.99. Found: C, 54.28; H, 5.03; N, 19.06.

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.
[2]Patent: US6498163,2002,B1 .
[3]Patent: US2004/224958,2004,A1 .

14
[ 107-08-4 ]
[ 211244-81-4 ]
[ 352359-90-1 ]

Yield	Reaction Conditions	Operation in experiment
97%		Example 274 2-Methylsulfanyl-8-propyl-8H-pyrido[2,3-d]pyrimidin-7-one The title compound was prepared from <strong>[211244-81-4]2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (10 g, 51.7 mmol) and iodopropane (5.5 mL, 57 mmol) by using the procedure described in Example 272 (Yield 97%). MS(CI) 236 MH+.

References: [1]Patent: US2004/224958,2004,A1 .
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

15
[ 62-53-3 ]
[ 211244-81-4 ]
[ 211244-93-8 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

16
[ 211244-81-4 ]
[ 211244-91-6 ]

Yield	Reaction Conditions	Operation in experiment
43%	With oxyaziridine; In methanol; dichloromethane; at 20℃;	EXAMPLE 52-MethanesuIfinyl-8H-pyrido[2,3-d]pyrimidin-7-one; To a suspension of <strong>[211244-81-4]2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (WO 9833798 A2, 5.0 g, 25.9 mmol) in CH2Cl2 (100 mL), CHCl3 (50 mL) and MeOH (10 mL, the starting material still did not dissolve) was added the oxaziridine (8.11 g, 31.05 mmol, 1.2 equiv) as a solid. The reaction became homogenous after 3 h and was stirred overnight at RT. The reaction was concentrated and CH2Cl2ZMeOH was added to dissolve the residue. Much of the solid did not dissolve so the mixture was filtered to give 2-Methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one, as an off-white solid (2.31 g, 11.04 mmol, 43%). MS: APCI: M+l: 210.1 (Exact Mass: 209.03).

References: [1]Patent: WO2006/90272,2006,A1 .Location in patent: Page/Page column 34.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

17
(E)-ethyl-3-(4-amino-2-(methylthio)pyrimidin-5-yl)acrylic acid [ No CAS ]
[ 211244-81-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium methylate; In methanol; at 80℃; for 6h;	The (E) - ethyl-3- (4-amino-2- (methylthio) pyrimidin-5-yl) acrylic acid (14g) (4-a are as defined in formulaThe compound shown) was dissolved in methanol (200ml), was added a solution of sodium methoxide in methanol (21mL), 80 stirredThe reaction 6h. After completion of the reaction the solvent was evaporated, water was added to dissolve with 2N hydrochloric acid and adjusted to pH = 8, producingLarge amount of deposits was filtered to give a white solid (8g, 73%) (4-b as shown in the formula compound):

References: [1]Patent: CN105481858,2016,A .Location in patent: Paragraph 0170; 0173; 0174.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.

18
[ 211244-81-4 ]
[ 74-88-4 ]
[ 211244-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	(6) To a suspension of the compound (103 mg) obtained in (5) above in dry dimethylformamide (3 ml) is added iodomethyl (37 mul) in ice bath using microsyringe, followed by addition of potassium carbonate powder (81 mg) in one portion. The reaction mixture is stirred at 0 C for 30 minutes, and then at room temperature for 30 minutes. After addition of water to the reaction mixture, the mixture is extracted with ethyl acetate. The organic layer is washed successively with water and brine, dried over sodium sulfate, and concentrated in vacuo to give a colorless solid. The resultant crude product is suspended in a mixed solvent of ethyl acetate and diisopropyl ether. The solids are collected by filtration, washed with a mixture of diisopropyl ether and hexane to give 2-methylthio-8-N-methyl-7, 8-dihydro-7-oxo-pyrido[2,3-d]pyrimidine (82 mg) as colorless powder. M.p. 192-193 C, MS (m/z) : 208 (MH+). IR (nujol): 1677, 1569, 1459, 1369, 1173 cm-1.

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.
[2]Patent: EP1364950,2003,A1 .Location in patent: Page/Page column 23.

19
[ 211244-81-4 ]
[ 352328-87-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With bromine; acetic acid; at 20℃; for 48h;	2-methylthio-pyrido [2,3-d] pyrimidin-7-one (300mg) (as shown in the formula the compound 4-b) dispersingIn glacial acetic acid (10ml), was added bromine (0.16mL), the reaction mixture was stirred at room temperature 48h. After completion of the reactionDichloromethane was added, filtered, washed with methanol to give a white solid (390mg, 92%) (as defined in formulaThe compound represented by 4-c):
48%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	To a solution of <strong>[211244-81-4]2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one</strong> (1.00 g, 5.18 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.59 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.50 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NuMR (400 MHz, DMSO-J6) delta ppm 12.88 (br. S., 1 H), 8.84 (s, 1 H), 8.47 (s, 1 H), 2.57 (s, 3H).
48%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h;	Step 1: Synthesis of 6-bromo-2-(methylthio)pyrido [2,3-d] pyrimidin-7(8H)-one (14).[00387] To a solution of <strong>[211244-81-4]2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one</strong> (8, 1.00 g, 5.2 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.6 mmol) in small portions at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.5 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NMR (400 MHz, DMSO- 6) delta ppm 12.88 (br. s., 1H), 8.84 (s, 1H), 8.47 (s, 1H), 2.57 (s, 3H).

48%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h;	Step 1: Synthesis of 6-bromo-<strong>[211244-81-4]2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one</strong> (2).[00378] To a solution of <strong>[211244-81-4]2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one</strong> (1, 1.00 g, 5.18 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.59 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.50 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NMR (400 MHz, DMSO- 6) delta ppm 12.88 (br. s., 1H), 8.84 (s, 1H), 8.47 (s, 1H), 2.57 (s, 3H).
48%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h;	Step 1: Synthesis of 6-bromo-<strong>[211244-81-4]2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one</strong> (7)·[00372] To a solution of <strong>[211244-81-4]2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one</strong> (6, 1.00 g, 5.2 mmol) in anhydrous dimethylformamide (25 mL) was added A jromosuccinimide (0.99 g, 5.6 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.5 mmol, 48%). ESMS m/z 272 (M+H)+; ¾ NMR (400 MHz, DMSO-<¾ delta ppm 12.88 (br. s, 1H), 8.84 (s, 1H), 8.47 (s, 1H), 2.57 (s, 3H).
48%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h;	To a solution of <strong>[211244-81-4]2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one</strong> (1, 1.00 g, 5.18 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.59 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.50 mmol, 48%). ESMS m/z 272 (M+H)+; ? NMR (400 MHz, DMSO-c/6) delta ppm 12.88 (br. s., 1 H), 8.84 (s, 1 H), 8.47 (s, 1H), 2.57 (s, 3H).
48%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h;	[00485] To a solution of <strong>[211244-81-4]2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (1) (1.00 g, 5.18 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.59 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.50 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NMR (400 MHz, DMSO-d6) delta ppm 12.88 (br. s., 1H), 8.84 (s, 1H), 8.47 (s, 1H), 2.57 (s, 3H).
5.59 g (79.4%)	With N-Bromosuccinimide; In N,N-dimethyl-formamide;	EXAMPLE 73 6-Bromo-<strong>[211244-81-4]2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> To 5.00 g (25.9 mmol) of 2-methanesulfanyl-8H-pyrido(2,3-d]pyrimidin-7-one (Example 5) in 130 mL of DMF is added 5.00 g (28.1 mmol) of N-bromosuccinimide. The resulting suspension is stirred at room temperature overnight and concentrated. The solid is triturated with hot water, then washed with isopropanol to give 5.59 g (79.4%) of the product as a solid. mp 266-270 C.

References: [1]Patent: CN105481858,2016,A .Location in patent: Paragraph 0170; 0175; 0176.
[2]Patent: WO2010/71846,2010,A2 .Location in patent: Page/Page column 185.
[3]Patent: WO2011/156780,2011,A2 .Location in patent: Page/Page column 138-139.
[4]Patent: WO2011/156646,2011,A2 .Location in patent: Page/Page column 134.
[5]Patent: WO2011/156786,2011,A2 .Location in patent: Page/Page column 129-130.
[6]Patent: WO2013/43232,2013,A2 .Location in patent: Paragraph 00491; 00492.
[7]Patent: WO2013/86451,2013,A2 .Location in patent: Paragraph 00485; 00503.
[8]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.
[9]Patent: US2003/73668,2003,A1 .

20
[ 211244-81-4 ]
[ 851756-48-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

21
[ 211244-81-4 ]
6-bromo-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

22
[ 211244-81-4 ]
[ 851756-49-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

23
[ 211244-81-4 ]
6-(2,6-dimethyl-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

24
[ 211244-81-4 ]
[ 851756-74-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

25
[ 211244-81-4 ]
6-(2-hydroxy-6-methoxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

26
[ 211244-81-4 ]
6-(2,6-difluoro-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

27
[ 211244-81-4 ]
6-(2-chloro-6-hydroxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

28
[ 211244-81-4 ]
6-(2,6-dihydroxy-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

29
[ 211244-81-4 ]
[ 851756-70-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

30
[ 211244-81-4 ]
[ 851756-92-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

31
[ 211244-81-4 ]
6-(4-hydroxy-2,6-dimethyl-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1931 - 1935.

32
[ 770-31-0 ]
[ 211244-81-4 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 413 - 418.
[3]Patent: CN105481858,2016,A .

33
[ 588-36-3 ]
[ 211244-81-4 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 413 - 418.

34
[ 5909-24-0 ]
[ 211244-81-4 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 413 - 418.

35
[ 776-53-4 ]
[ 211244-81-4 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4606 - 4616.
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 413 - 418.

Historical Records

Technical Information

• Acyl Group Substitution • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Lawesson's Reagent • Nucleophilicity of Sulfur Compounds • Oxidation States of Sulfur Compounds • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes

Related Functional Groups of
[ 211244-81-4 ]

Amides

A101628 [1013916-37-4]

2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one

Similarity: 0.67

A310645 [902576-09-4]

2-(Methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one

Similarity: 0.65

A193690 [59341-68-3]

6-Methyl-2-(pyridin-4-yl)pyrimidin-4(3H)-one

Similarity: 0.63

A202610 [1211443-61-6]

2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Similarity: 0.60

A827549 [1290541-46-6]

(E)-3-Benzyl-2-(2-(pyridin-3-yl)vinyl)quinazolin-4(3H)-one

Similarity: 0.60

Sulfides

A175498 [185040-32-8]

4-(Methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Similarity: 0.73

A509409 [57564-94-0]

4-Chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.69

A659647 [211230-35-2]

Ethyl 4-((4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate

Similarity: 0.68

A160341 [770-31-0]

4-Amino-2-(methylthio)pyrimidine-5-carbaldehyde

Similarity: 0.67

A197459 [1268522-00-4]

4-Amino-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde

Similarity: 0.66

Related Parent Nucleus of
[ 211244-81-4 ]

Other Aromatic Heterocycles

A509409 [57564-94-0]

4-Chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.69

A101628 [1013916-37-4]

2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one

Similarity: 0.67

A310645 [902576-09-4]

2-(Methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one

Similarity: 0.65

A202610 [1211443-61-6]

2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Similarity: 0.60

A432404 [1016636-76-2]

6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one

Similarity: 0.59

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P283	Wear fire/flame resistant/retardant clothing.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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.: 211244-81-4

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