Home Cart Sign in  
Chemical Structure| 96833-41-9 Chemical Structure| 96833-41-9

Structure of 96833-41-9

Chemical Structure| 96833-41-9

2-Chloro-4-methoxypyrimidin-5-amine

CAS No.: 96833-41-9

4.5 *For Research Use Only !

Cat. No.: A152007 Purity: 97%

Change View

Size Price

US Stock

Global Stock

In Stock
100mg łËď¶ÊÊ Inquiry Inquiry
250mg ł§§¶ÊÊ Inquiry Inquiry
1g łÍÿ¶ÊÊ Inquiry Inquiry
5g łÇóʶÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 100mg

    łËď¶ÊÊ

  • 250mg

    ł§§¶ÊÊ

  • 1g

    łÍÿ¶ÊÊ

  • 5g

    łÇóʶÊÊ

In Stock

- +

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 [ 96833-41-9 ]

CAS No. :96833-41-9
Formula : C5H6ClN3O
M.W : 159.57
SMILES Code : NC1=CN=C(Cl)N=C1OC
MDL No. :MFCD12402341
InChI Key :BTTZBKYSXZSBAS-UHFFFAOYSA-N
Pubchem ID :21186356

Safety of [ 96833-41-9 ]

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

Computational Chemistry of [ 96833-41-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 37.94
TPSA ?

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

61.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.66
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

0.79
Log Po/w (WLOGP)?

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

0.73
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.

-0.25
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

0.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.76

Water Solubility

Log S (ESOL):?

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

-1.71
Solubility 3.15 mg/ml ; 0.0197 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.

-1.65
Solubility 3.55 mg/ml ; 0.0223 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

-2.02
Solubility 1.51 mg/ml ; 0.00944 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.

-6.71 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)

2.01

Application In Synthesis of [ 96833-41-9 ]

* 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.

  • Upstream synthesis route of [ 96833-41-9 ]
  • Downstream synthetic route of [ 96833-41-9 ]

[ 96833-41-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 5177-27-5 ]
  • [ 124-41-4 ]
  • [ 96833-41-9 ]
YieldReaction ConditionsOperation in experiment
91% at 20℃; for 1.5 h; Preparation 164
2-Chloro-4-methoxypyrimidin-5-amine
Sodium methoxide (0.5M in methanol, 3.7 mL, 1.829 mmol) was added to a solution of 2,4-dichloropyrimidin-5-amine (0.2 g, 1.220 mmol) in MeOH (2.5 mL).
The reaction was stirred at room temperature for 1.5 hours.
The reaction was then diluted with EtOAc and quenched with water.
The layers were separated and the aqueous layer was extracted with EtOAc.
The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title product as a brown solid (177 mg, 91percent).
1H NMR (500 MHz, CDCl3): δ 3.93 (s, 3H), 5.31 (br s, 2H), 7.73 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 1.6 min, 160 [M+H]+
83% at 0 - 20℃; for 66 h; Inert atmosphere 5.4Msodium methoxide (100 μ, 0.54 mmol) was added dropwise to a stirring solutionof 2,4-dichloropyrimidin-5 -amine (89 mg, 0.54 mmol) in methanol (2 mL) at 0 °Cunder nitrogen. The reaction was allowed to warm to room temperature andstirred for 1 hr. The reaction was treated with more 5.4M sodium methoxide (10μ) and stirred for a further 1 hr, then left to stand at room temperature for64 hrs. The reaction was quenched with acetic acid (1 mL) and concentrated invacuo. The residue was dissolved in EtOAc (20 mL) and washed with saturatedaqueous NaHC03 (2 x 6 mL), brine (6 mL), dried over Na2SC>4,filtered and the filtrate was concentrated in vacuo. The residue obtained waspurified by flash column chromatography over silica (Biotage 10 g SNAPcartridge) eluting with heptane:EtOAc , smooth gradient 1 :0 to 7:3 to affordthe title compound as a white solid (80 mg, 83percent) ; H NMR (500 MHz,DMSO) δ 3.93 (s, 3H), 5.31 (s, 2H), 7.72 (s, 1H).
0.35 g for 16 h; Reflux A mixture of 2,4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25percent ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.
References: [1] Patent: US2013/345181, 2013, A1, . Location in patent: Paragraph 0785.
[2] Patent: WO2014/184234, 2014, A1, . Location in patent: Page/Page column 71; 72.
[3] Patent: WO2014/191632, 2014, A1, . Location in patent: Page/Page column 56.
  • 2
  • [ 67-56-1 ]
  • [ 5177-27-5 ]
  • [ 124-41-4 ]
  • [ 96833-41-9 ]
YieldReaction ConditionsOperation in experiment
91% at 20℃; for 1.5 h; Preparation 164: 2-Chloro-4-methoxypyrimidin-5-amine; [00336] Sodium methoxide (0.5M in methanol, 3.7ml_, 1 .829mmol) was added to a solution of 2,4-dichloropyrimidin-5-amine (0.2g, 1 .220mmol) in MeOH (2.5ml_). The reaction was stirred at room temperature for 1 .5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure to afford the title product as a brown solid (177mg, 91 percent).1 H NMR (500MHz, CDCI3): δ 3.93 (s, 3H), 5.31 (br s, 2H), 7.73 (s, 1 H). LC (Method B)-MS (ESI, m/z) fR 1 .6 min, 160 [M+H]+
References: [1] Patent: WO2012/123745, 2012, A1, . Location in patent: Page/Page column 117.
  • 3
  • [ 5177-27-5 ]
  • [ 96833-41-9 ]
References: [1] Patent: US5861401, 1999, A, .
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 96833-41-9 ]

Chlorides

Chemical Structure| 22536-63-6

A145201 [22536-63-6]

2-Chloro-4-methoxypyrimidine

Similarity: 0.83

Chemical Structure| 22536-64-7

A155810 [22536-64-7]

2-Chloro-4-methoxy-6-methylpyrimidine

Similarity: 0.78

Chemical Structure| 1445894-94-9

A206180 [1445894-94-9]

2-Chloro-4-isopropoxy-5-nitropyrimidine

Similarity: 0.75

Chemical Structure| 56621-90-0

A200494 [56621-90-0]

5-Amino-2-chloropyrimidine

Similarity: 0.70

Chemical Structure| 18214-00-1

A102887 [18214-00-1]

2-Chloro-4-phenoxypyrimidine

Similarity: 0.69

Ethers

Chemical Structure| 22536-63-6

A145201 [22536-63-6]

2-Chloro-4-methoxypyrimidine

Similarity: 0.83

Chemical Structure| 55150-17-9

A323713 [55150-17-9]

4-Ethoxypyrimidin-5-amine

Similarity: 0.79

Chemical Structure| 22536-64-7

A155810 [22536-64-7]

2-Chloro-4-methoxy-6-methylpyrimidine

Similarity: 0.78

Chemical Structure| 1445894-94-9

A206180 [1445894-94-9]

2-Chloro-4-isopropoxy-5-nitropyrimidine

Similarity: 0.75

Chemical Structure| 53135-45-8

A124763 [53135-45-8]

4-Methoxy-2-methylpyrimidin-5-amine

Similarity: 0.73

Amines

Chemical Structure| 55150-17-9

A323713 [55150-17-9]

4-Ethoxypyrimidin-5-amine

Similarity: 0.79

Chemical Structure| 53135-45-8

A124763 [53135-45-8]

4-Methoxy-2-methylpyrimidin-5-amine

Similarity: 0.73

Chemical Structure| 14048-15-8

A203765 [14048-15-8]

2,4-Dimethoxypyrimidin-5-amine

Similarity: 0.71

Chemical Structure| 56621-90-0

A200494 [56621-90-0]

5-Amino-2-chloropyrimidine

Similarity: 0.70

Chemical Structure| 943314-62-3

A124266 [943314-62-3]

3-((2-Chloropyrimidin-4-yl)oxy)aniline

Similarity: 0.68

Related Parent Nucleus of
[ 96833-41-9 ]

Pyrimidines

Chemical Structure| 22536-63-6

A145201 [22536-63-6]

2-Chloro-4-methoxypyrimidine

Similarity: 0.83

Chemical Structure| 55150-17-9

A323713 [55150-17-9]

4-Ethoxypyrimidin-5-amine

Similarity: 0.79

Chemical Structure| 22536-64-7

A155810 [22536-64-7]

2-Chloro-4-methoxy-6-methylpyrimidine

Similarity: 0.78

Chemical Structure| 1445894-94-9

A206180 [1445894-94-9]

2-Chloro-4-isopropoxy-5-nitropyrimidine

Similarity: 0.75

Chemical Structure| 53135-45-8

A124763 [53135-45-8]

4-Methoxy-2-methylpyrimidin-5-amine

Similarity: 0.73