908240-50-6|2,4-Dichloropyrido[3,4-d]pyrimidine| 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 [ 908240-50-6 ] Purity: 95% 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 [ 908240-50-6 ]

CAS No. :	908240-50-6
Formula :	C₇H₃Cl₂N₃
M.W :	200.02
SMILES Code :	ClC1=NC2=C(C=CN=C2)C(Cl)=N1
MDL No. :	MFCD10699461
InChI Key :	YJUVYWACDUJBDG-UHFFFAOYSA-N
Pubchem ID :	45789969

Safety of [ 908240-50-6 ]

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

Computational Chemistry of [ 908240-50-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	47.35
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.67 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.9
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	2.39
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.33
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.	1.25
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	2.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.12

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.2
Solubility	0.125 mg/ml ; 0.000627 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.	-2.84
Solubility	0.287 mg/ml ; 0.00143 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	-4.19
Solubility	0.0128 mg/ml ; 0.0000641 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	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.	-5.82 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	0.0
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)	1.68

Application In Synthesis of [ 908240-50-6 ]

* 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 [ 908240-50-6 ]

[ 908240-50-6 ] Synthesis Path-Downstream 1~35

2
[ 110-91-8 ]
[ 908240-50-6 ]
C₁₁H₁₁ClN₄O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5950 - 5953.

3
C₇H₄N₃O₂^(1-)*K⁽¹⁺⁾ [ No CAS ]
[ 908240-50-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5950 - 5953.

4
[ 908240-50-6 ]
[ 98-80-6 ]
[ 1262866-86-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 3h;	After 2,4-dichloropyrido[3,4-d]pyrimidin (5 g, 24.9 mmol), phenylboronic acid (3.6 g, 29.9 mmol), Pd(PPh3)4 (1/15 g, 0.996 mmol), sodium carbonate aqueous solution (87 mL) , and ethanol (87 mL) were dissolved in toluene (180 mL), the mixture was stirred under reflux at 120 C for 3 hours. When the reaction was completed, an organic layer was extracted with ethyl acetate and remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound B-I (4 g, 16.5 mmol, 67 percent)

References: [1]Patent: WO2011/14039,2011,A1 .Location in patent: Page/Page column 20.
[2]Organic Letters,2017,vol. 19,p. 6368 - 6371.

5
[ 908240-50-6 ]
[ 98-80-6 ]
[ 1262866-87-4 ]

References: [1]Patent: WO2011/14039,2011,A1 .

6
[ 3731-53-1 ]
[ 908240-50-6 ]
[ 1352995-30-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	2-Chloro-N-(pyridin-4-ylmethyl)pyrido[3,4-d]pyrimidin-4-amine (B-3)To a solution of B-2 (500 mg, 2.50 mmol) in 12.5 mL of anhydrous DMF at RT under N2 was added 4-(aminomethyl)pyridine (0.278 mL, 2.75 mmol) followed by triethylamine (523 muL, 3.75 mmol). After stirring for several hours, the mixture was diluted with sat. aqueous NaHCO3 solution and extracted several times with EtOAc. The organic layers were combined and washed with sat. aqueous NaHCO3 solution, water, then brine, then dried with Na2SO4 and concentrated. The aqueous layers were combined and reextracted several times with 4:1 CHCl3-isopropanol; the organic layers were combined with the EtOAc extraction and concentrated. The residue was adsorbed onto silica gel and then purified by gradient elution on silica gel (0 to 100percent (25percent 20:1:1 EtOH:NH4OH:H2O-75percent EtOAc) in hexanes) to yield 426 mg (63percent) of B-3 as a dark brown solid. Data for B-3: 1HNMR (500 MHz, DMSO-d6) delta 9.71 (m, 1H), 9.05 (s, 1H), 8.68 (d, 1H), 8.52 (d, 2H), 8.20 (d, 1H), 7.37 (d, 2H), 4.80 (d, 2H) ppm. HRMS (ES) calculated M+H for C13H11ClN5: 272.0698. Found: 272.0696.

References: [1]Patent: US2011/319409,2011,A1 .Location in patent: Page/Page column 18.

7
2-thioxo-2,3-dihydropyrido[3,4-d]-pyrimidin-4(1H)-one [ No CAS ]
[ 908240-50-6 ]

Yield	Reaction Conditions	Operation in experiment
27%		2,4-Dichloropyrido[3,4-d]pyrimidine (B-2)To a suspension of B-1 (500 mg, 2.8 mmol) in 6.5 mL (70 mmol) POCl3 was added DMF (32 muL, 0.4 mmol) and the mixture was heated in the microwave at 130° C. for 10 minutes. The reaction was transferred to a 250 mL round bottom flask with the help of DCM, and the volatiles were removed by rotary evaporation. The residue was suspended in 75 mL DCM and to this was carefully added 75 mL of 5percent aqueous Na2CO3 (pH>10 after addition). The layers were separated with the help of additional DCM, the organic was washed with water, dried over Na2SO4, and concentrated to provide 367 mg of a brown solid. This material was dissolved in DCM, dry loaded onto silica gel, and purified by column chromatography (0 to 100percent EtOAc in hexanes) to provide 148 mg (27percent) of B-2 as a white solid. Data for B-2: 1HNMR (500 MHz, CDCl3) delta 12.9 (s, 1H), 12.7 (s, 1H), 8.7 (s, 1H), 8.5 (d, 1H), 7.75 (d, 1H) ppm.

References: [1]Patent: US2011/319409,2011,A1 .Location in patent: Page/Page column 18.

8
[ 21038-67-5 ]
[ 908240-50-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; at 25℃; for 18h;	To a mixture of pyrido[3,4-d]pyrimidine-2,4(1 H,3H)-dione (2b, 20.00 g, 122.60 mmol) and POCI3 (328.03 g, 2.14 mol) in toluene (200 mL) was added DIEA (31 .69 g, 245.20 mmol) dropwise and this reaction mixture stirred at 25°C overnight (18hr) to give suspension. The solvent and POCI3 was removed under vacuum, diluted with DCM (50 mL), neutralized with DIEA to pH=7 at -20°C and concentrated again, the residue was purified by column (20-50percent EA/PE) to give the product (2c, 20.00g, 99.99 mmol, 82percent yield) as a yellow solid. 1 H NMR (400 MHz, CHLOROFORM-d) delta 9.52 (s, 1 H), 8.92 (d, J=5.6 Hz, 1 H), 8.04 (d, J=5.6 Hz, 1 H). LCMS (m/z [M+H]+): 200.0.
41%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene;Reflux;	To a mixture of pyrido[3,4-d]pyridine-2,4(1H,3H)-dione (2.0 g, 12.3 mmol) in toluene (50 mL) was added DIEA (3.15 g, 25 mmol) and POC13 (9.5 g, 61.4 mmol). The reaction mixture was refluxed overnight. The solution was concentrated in vacuo and the residue was taken in ethyl acetate, washed with aq. NaHCO3 and brine. The organics were dried and concentrated. The residue was purified by silica gel chromatography (25percent EA:PE)to give 1.0 g (41percent) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 9.50 (s, 1H), 8.90 (d, 1H, J 5.2 Hz), 8.02 (d, 1H, J 5.2 Hz).
41%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene;Reflux;	[00156j To a mixture of pyrido[3,4-d]pyridine-2,4(1H,3H)-dione (2 g, 12.3 mmol) in toluene (50 mL) was added DIEA (3.15 g, 25 mmol) and POC13 (9.5 g, 61.4 mmol). The reaction mixture was refluxed overnight. The solution was concentrated in vacuo and the residue was taken in ethyl acetate and washed with aq. NaHCO3 and brine. The organics were dried and concentrated. The residue was purified by silica gel chromatography (25percent EA:PE) to afford lg (4 1percent) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 9.50 (s, 1H), 8.90 (d, 1H, J 5.2Hz), 8.02 (d, 1H, J 5.2Hz).

References: [1]Patent: WO2018/198077,2018,A2 .Location in patent: Page/Page column 189; 197; 225; 226; 262; 263.
[2]Patent: WO2014/151106,2014,A1 .Location in patent: Paragraph 00109.
[3]Patent: WO2016/44429,2016,A1 .Location in patent: Paragraph 00154; 00156.

9
[ 64188-97-2 ]
[ 908240-50-6 ]