Home Cart Sign in  
Chemical Structure| 1189169-37-6 Chemical Structure| 1189169-37-6

Structure of 1189169-37-6

Chemical Structure| 1189169-37-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1189169-37-6 ]

CAS No. :1189169-37-6
Formula : C6H5BrN2O
M.W : 201.02
SMILES Code : CC(C1=NC=C(Br)C=N1)=O
MDL No. :MFCD18909512
InChI Key :NZGSEUQFYKCKRU-UHFFFAOYSA-N
Pubchem ID :53488064

Safety of [ 1189169-37-6 ]

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

Computational Chemistry of [ 1189169-37-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 39.93
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

42.85 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.54
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.91
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.44
Log Po/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.

0.09
Log Po/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

1.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.17

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.04
Solubility 1.84 mg/ml ; 0.00917 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.

-1.4
Solubility 8.09 mg/ml ; 0.0402 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

-2.85
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

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.

-6.88 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)

1.57

Application In Synthesis of [ 1189169-37-6 ]

* 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.

  • Upstream synthesis route of [ 1189169-37-6 ]

[ 1189169-37-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1072-97-5 ]
  • [ 97674-02-7 ]
  • [ 1189169-37-6 ]
YieldReaction ConditionsOperation in experiment
66% With bis-triphenylphosphine-palladium(II) chloride In toluene at 130℃; for 16 h; Inert atmosphere 5-Bromo-2-iodopyrimidine (10 g, 35.1 mmol) and tributyl(1-ethoxyethenyl)- stannane (15.85 g, 43.88 mmol) were dissolved in anhydrous toluene (500 mL) and purged with nitrogen for 10 minutes. Dichlorobis(triphenylphosphine)palladium(II) (1.23 g, 1.76 mmol) was added and the mixture was stirred at 130°C for 16 h. The reaction mixture was cooled to room temperature and water (29 mL) was added, followed by 6MHC1 (106 mL), then the mixture was stirred vigorously at room temperature for 4 h. The solvent was removed in vacuo and the pH of the mixture was adjusted to pH 7 by the addition of saturated aqueous sodium hydrogencarbonate solution (500 mL). The mixture was extracted with ethyl acetate (3 x 350 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material waspurified on silica gel, eluting with 20-100percent ethyl acetate in heptane, to afford the title compound (2.99 g, 66 percent) as a gold-coloured solid. LCMS m/z 20 1/203.
References: [1] Patent: WO2015/86506, 2015, A1, . Location in patent: Page/Page column 125.
  • 2
  • [ 97674-02-7 ]
  • [ 183438-24-6 ]
  • [ 1189169-37-6 ]
YieldReaction ConditionsOperation in experiment
70% With bis-triphenylphosphine-palladium(II) chloride In toluene at 130℃; for 18 h; Inert atmosphere 5-bromo-2-iodopyrimidine (16 g, 56.16 mmol) and tributyl(l- ethoxyethenyl)stannane (25 g, 69.22 mmol) were dissolved in toluene (500 mL) and purged with N2for 10 mins. Palladium (2+) chloride - triphenylphosphane (1 :2:2) (3.5 g, 4.99 mmol) was added and the reaction mixture was heated at 130 °C for 18 h. The reaction was allowed to cool to r.t. Water (70 ml) and 6M HC1 (280 ml) were added and - -the reaction mixture was allowed to stir vigorously for 4 h. The pH of the mixture was adjusted to pH 7 by the addition of saturated aqueous Na2C03(approximately 300 mL) and the mixture extracted with EtOAc (3 x 350 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (Si02, 20-100percent EtOAc in Heptane) to afford the title compound as a golden-yellow solid (7.9 g,70percent). 1H NMR (500 MHz, CDC13) δ 8.97 (s, 2H), 2.77 (s, 3H).
References: [1] Patent: WO2015/86526, 2015, A1, . Location in patent: Page/Page column 153; 154.
  • 3
  • [ 75-16-1 ]
  • [ 38275-57-9 ]
  • [ 1189169-37-6 ]
YieldReaction ConditionsOperation in experiment
61% at -78℃; for 3.5 h; 1-(5-Bromopyrimidin-2-yl)ethanone
To a solution of 5-bromopyrimidine-2-carbonitrile (221 mg, 1.2 mmol) in THF (10 ml) was added methylmagnesium bromide (3.0 ml, 4.20 mmol, 1.4 molar, THF) at -78° C. under nitrogen.
The solution was stirred at -78° C. for 3.5 hours, and then quenched with satd aq NH4Cl, and extracted with EtOAc.
The combined organic layer was dried over anhydrous Na2SO4 and concentrated.
The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 1-(5-bromopyrimidin-2-yl)ethanone (1.55 mg, 61percent yield).
1H NMR (CDCl3 500 MHz): δ 9.00 (s, 2H), 2.80 (s, 3H).
References: [1] Patent: US2014/107335, 2014, A1, . Location in patent: Paragraph 0172; 0173.
[2] Patent: WO2018/97945, 2018, A1, . Location in patent: Paragraph 0528.
[3] Patent: US2009/253708, 2009, A1, . Location in patent: Page/Page column 15.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 1189169-37-6 ]

Bromides

Chemical Structure| 1346808-91-0

A111908 [1346808-91-0]

1-(5-Bromopyrimidin-2-yl)propan-1-one

Similarity: 0.93

Chemical Structure| 873331-73-8

A121125 [873331-73-8]

5-Bromo-2-ethylpyrimidine

Similarity: 0.81

Chemical Structure| 1060813-04-8

A149531 [1060813-04-8]

5-Bromo-2-isopropylpyrimidine

Similarity: 0.77

Chemical Structure| 831203-15-7

A129868 [831203-15-7]

2-(5-Bromopyrimidin-2-yl)acetonitrile

Similarity: 0.75

Chemical Structure| 1134327-93-7

A378410 [1134327-93-7]

2-(5-Bromopyrimidin-2-yl)acetic acid

Similarity: 0.74

Ketones

Chemical Structure| 1346808-91-0

A111908 [1346808-91-0]

1-(5-Bromopyrimidin-2-yl)propan-1-one

Similarity: 0.93

Chemical Structure| 53342-27-1

A165888 [53342-27-1]

1-(2-Pyrimidinyl)ethanone

Similarity: 0.82

Chemical Structure| 905587-44-2

A118355 [905587-44-2]

1-(5-Fluoropyrimidin-2-yl)ethanone

Similarity: 0.72

Chemical Structure| 1245643-85-9

A310812 [1245643-85-9]

1-(5-Bromopyrimidin-4-yl)ethanone

Similarity: 0.63

Chemical Structure| 39870-05-8

A151841 [39870-05-8]

1-(Pyrimidin-4-yl)ethanone

Similarity: 0.54

Related Parent Nucleus of
[ 1189169-37-6 ]

Pyrimidines

Chemical Structure| 1346808-91-0

A111908 [1346808-91-0]

1-(5-Bromopyrimidin-2-yl)propan-1-one

Similarity: 0.93

Chemical Structure| 53342-27-1

A165888 [53342-27-1]

1-(2-Pyrimidinyl)ethanone

Similarity: 0.82

Chemical Structure| 873331-73-8

A121125 [873331-73-8]

5-Bromo-2-ethylpyrimidine

Similarity: 0.81

Chemical Structure| 1060813-04-8

A149531 [1060813-04-8]

5-Bromo-2-isopropylpyrimidine

Similarity: 0.77

Chemical Structure| 831203-15-7

A129868 [831203-15-7]

2-(5-Bromopyrimidin-2-yl)acetonitrile

Similarity: 0.75