1266343-30-9|5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine| Ambeed

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Quality Control of [ 1266343-30-9 ] Purity: 95% SDS Specification

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Product Details of [ 1266343-30-9 ]

CAS No. :	1266343-30-9
Formula :	C₇H₅BrClN₃
M.W :	246.49
SMILES Code :	CN1C=C(Br)C2=C(Cl)N=CN=C12
MDL No. :	MFCD14635647
InChI Key :	QGPYXNYRUAFOHC-UHFFFAOYSA-N
Pubchem ID :	66545160

Safety of [ 1266343-30-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P280

Computational Chemistry of [ 1266343-30-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	51.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	30.71 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.26
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	2.27
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.38
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.	1.85
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	2.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.35
Solubility	0.109 mg/ml ; 0.000443 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.	-2.55
Solubility	0.692 mg/ml ; 0.00281 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	-3.57
Solubility	0.0657 mg/ml ; 0.000267 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	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.	-6.19 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)	1.64

Application In Synthesis of [ 1266343-30-9 ]

* 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 [ 1266343-30-9 ]

[ 1266343-30-9 ] Synthesis Path-Downstream 1~35

1
[ 124-38-9 ]
[ 1266343-30-9 ]
[ 1069473-61-5 ]

Yield	Reaction Conditions	Operation in experiment
87%		STEP 2: 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid [Chem. 4]To a stirred solution of <strong>[1266343-30-9]5-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine</strong> (STEP 1, 8.20 g, 33.3 mmol) in tetrahydrofuran (120 mL) was added 1.59 M n-butyllithium in hexane solution (25.1 mL, 39.9 mmol) slowly at -78 oC. After stirring at -78 oC for 1 hr, solid CO2 was added to the mixture. The resulting was warmed to room temperature gradually, and quenched with 1M HCl aqueous solution (200 mL). The mixture was extracted with dichloromethane/methanol (10/1, 200 mLx4), and the combined organic fraction was dried over magnesium sulfate. After removal of the solvent by evaporation, the residue was triturated with ethyl acetate (100 mL) and collected by filtration to give the title compound (6.11 g, 87%) as an off-white solid.;LCMS (Method A) m/z: M+1 212.0; tR = 1.30 min.

References: [1]Patent: WO2011/18894,2011,A1 .Location in patent: Page/Page column 26.

2
[ 7781-10-4 ]
[ 1266343-30-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; In dichloromethane; at 0 - 25℃; for 2.0h;	Example 1 5-(1H-1,3-Benzodiazol-2-yl)-7-methyl-N-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine[0122]STEP 1: 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine [Chem. 3]To a stirred solution of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (WO2005/095357, 6.02 g, 35.9 mmol) in dichloromethane (120 mL) was added N-bromosuccinimide (7.67 g, 43.1 mmol) at 0 oC. The resulting mixture was stirred at room temperature for 2 hrs. The reaction mixture was quenched with saturated sodium bicarbonate aqueous solution (200 mL), and extracted with dichloromethane (200 mL). The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (dichloromethane/ethyl acetate=10/1) to give the title compound (8.27 g, 93%) as a white solid.;LCMS (Method A) m/z: M+1 247.9; tR = 2.70 min.
86%	With N-Bromosuccinimide; In dichloromethane; at 15 - 23℃; for 3.0h;	Add N-bromosuccinimide (418 g, 2.35 mol) portionwise over 20 min at 15 C to a solution of 4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (355 g, 2.12 mol) indichloromethane (3.19 L), and stir at 23 C for 3 h. After this time, filter, wash with H20 (5.32 L), and dry to give the title compound (448 g, 86%) as a white solid. ES/MS m/z (35C1,79Br) 245.9 (M+H).
	With N-Bromosuccinimide; In dichloromethane; at 20℃;	5-bromo-4-chloro-7-methyl-7H-Dyrrolo[2,3-dlDyrimidineTo 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (12.15 g, 72.5 mmol) in Dichloromethane (DCM) (200 ml.) was added NBS (13.55 g, 76 mmol) portionwise, and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated, and the solid was washed with water and dried to afford 5-bromo-4-chloro-7- methyl-7H-pyrrolo[2,3-d]pyrimidine (17 g) as an off-white solid.

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7193 - 7207.
[2]Patent: WO2011/18894,2011,A1 .Location in patent: Page/Page column 25-26.
[3]Patent: WO2018/194885,2018,A1 .Location in patent: Page/Page column 16.
[4]Patent: WO2011/119663,2011,A1 .Location in patent: Page/Page column 82.
[5]MedChemComm,2014,vol. 5,p. 1500 - 1506.

3
[ 1266343-30-9 ]
[ 1266343-32-1 ]

References: [1]Patent: WO2011/18894,2011,A1 .

4
[ 1266343-30-9 ]
[ 1266343-34-3 ]

References: [1]Patent: WO2011/18894,2011,A1 .

5
[ 1266343-30-9 ]
[ 1266341-96-1 ]

References: [1]Patent: WO2011/18894,2011,A1 .

6
[ 3680-69-1 ]
[ 1266343-30-9 ]

References: [1]Patent: WO2011/119663,2011,A1 .
[2]MedChemComm,2014,vol. 5,p. 1500 - 1506.
[3]Patent: WO2018/194885,2018,A1 .

7
[ 1266343-30-9 ]
[ 1337530-96-7 ]

References: [1]Patent: WO2011/119663,2011,A1 .

8
[ 1266343-30-9 ]
[ 1337532-51-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With ammonium hydroxide; at 120℃; for 18.0h;	Stir a suspension of 5-bromo-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (454 g 1.84 mol) in ammonia (30% in H20, 3.63 L) at 120 C in a Hastelloy pressure vessel for 18 h. Cool to 20 C, filter, wash with H20 (1.80 L) and methanol (900 mL), and dry to give the title compound (351 g, 82%) as a white solid. ES/MS m/z (79Br) 227.2(M+H).
	With ammonium hydroxide; at 100℃; for 48.0h;Sealed vessel;	5-bromo- 7-meth yl- 7H-p yrrolo[2, 3-d ID yrimidin-4-amineA suspension of <strong>[1266343-30-9]5-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine</strong> (17 g, 69.0 mmol) in ammonium hydroxide (150 ml_, 3852 mmol) was stirred for 2 days at 100 C in a sealed vessel. The reaction was allowed to cool to room temperature and filtered. The collected solid was washed with Et20 to afford the product 5-bromo-7-methyl-7H-pyrrolo[2,3- d]pyrimidin-4-amine (12.5 g) as a white solid.

References: [1]Patent: WO2018/194885,2018,A1 .Location in patent: Page/Page column 16.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7193 - 7207.
[3]MedChemComm,2014,vol. 5,p. 1500 - 1506.
[4]Patent: WO2011/119663,2011,A1 .Location in patent: Page/Page column 82.

9
[ 1266343-30-9 ]
[ 1337533-33-1 ]

References: [1]Patent: WO2011/119663,2011,A1 .

10
[ 1266343-30-9 ]
[ 1337533-34-2 ]

References: [1]Patent: WO2011/119663,2011,A1 .

11
[ 1266343-30-9 ]
[ 1337533-83-1 ]

References: [1]Patent: WO2011/119663,2011,A1 .

12
[ 1266343-30-9 ]
5-(4-chloro-2,3-dihydro-1H-indol-5-yI)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochloride [ No CAS ]

References: [1]Patent: WO2011/119663,2011,A1 .

13
[ 1266343-30-9 ]
[ 1337531-51-7 ]