Home Cart Sign in  
Chemical Structure| 5305-59-9 Chemical Structure| 5305-59-9

Structure of 4-Amino-6-chloropyrimidine
CAS No.: 5305-59-9

Chemical Structure| 5305-59-9

*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

DE Stock

US Stock

Asia 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) ]}

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

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

Alternative Products

Product Details of [ 5305-59-9 ]

CAS No. :5305-59-9
Formula : C4H4ClN3
M.W : 129.55
SMILES Code : C1=C(N=CN=C1N)Cl
MDL No. :MFCD00053576
InChI Key :DUKKRSPKJMHASP-UHFFFAOYSA-N
Pubchem ID :238012

Safety of [ 5305-59-9 ]

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

Computational Chemistry of [ 5305-59-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 31.45
TPSA ?

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

51.8 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.26
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

0.82
Log Po/w (WLOGP)?

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

0.72
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.

-0.05
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

0.98
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.75

Water Solubility

Log S (ESOL):?

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

-1.71
Solubility 2.5 mg/ml ; 0.0193 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.

-1.49
Solubility 4.19 mg/ml ; 0.0324 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

-1.87
Solubility 1.74 mg/ml ; 0.0135 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

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.

-6.51 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

2.0
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)

1.51

Application In Synthesis of [ 5305-59-9 ]

* 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 [ 5305-59-9 ]

[ 5305-59-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 5305-59-9 ]
  • [ 53557-69-0 ]
YieldReaction ConditionsOperation in experiment
70% With hydrogen iodide; sodium iodide; In water; at 70℃; for 0.5h; Description 93; 6-IodoPvrimidin-4-amine-«,; A mixture of 4-amino-6-chloropyrimidine [WO-A-0245652] (1. 00 g, 7.72 mmol), sodium iodide (5.79 g, 38.6 mmol) and 40% HI (20 ml) were heated at 70C for 30 min, then allowed to cool to room temperature. The precipitate was removed by filtration, and partitioned between dichloromethane and sat. NaHCO3. The organic layer was separated, and dried over Na2SO4, filtered, and evaporated to give the title compound (1.2 g, 70%). 1H NMR (400 MHz, DMSO-d6) 6.89 (1 H, s), 7.04 (2 H, br s), 8.04 (1 H, s).
65% With hydrogen iodide; In water; at 0 - 20℃; for 18.5h; 6-Chloropyrimidin-4-ylamine (450 mg) was added in portions to HI (57% wt. aq. , 20 mL) at 0 C. The reaction mixture was stirred for 30 minutes at 0 C and then at ambient temperature for 18 hours. The reaction mixture was treated with NaHC03 (sat. aq. ) until pH8 was achieved and then the product extracted with EtOAc (2 x 30 mL). The combined organics were washed with NaOH (2M, aq. ), dried (MgS04), filtered and then concentrated. The crude product was used directly without further purification (500 mg, 65%); lH NMR (CDCl3) ; 6.90 (s, 1H), 7.03 (s, 2H), 8.05 (s, 1H); MS m/e MHs 221.
47% With hydrogen iodide; In water; at 0 - 20℃; for 3.0h; General procedure: 2-Amino-4-chloropyrimidine (55) (13.0g, 100mmol) was added to a 57wt.% aqueous solution of hydriodic acid (115ml, 1.00mol) at 0C and the mixture was stirred at room temperature for 3h. The mixture was cooled to 0C and the resulting precipitate was removed by filtration and taken up in cold 5N aqueous Na2CO3 (200ml). The mixture was extracted with EtOAc (3×500ml) and the combined organic layers were concentrated under reduced pressure to deliver 2-amino-4-iodopyrimidine (21.1g, 95.0mmol, 95% yield) as a white solid.
  • 2
  • [ 5305-59-9 ]
  • [ 6092-47-3 ]
  • [ 865604-27-9 ]
YieldReaction ConditionsOperation in experiment
9% In 1,3-dimethyl-2-imidazolidinone; at 130℃; for 6.5h; A solution of 6-amino-4-chloropyrimidine (1) (0.504 g, 3.89 mmol) and N- <strong>[6092-47-3]chloroacetylurethane</strong> (0.770 g, 4.65 mmol) in 1, 3-dimethyl-2-imidazolidinone (10 mL) was heated to 130C under nitrogen for 3 h. N-Chloroacetylurethane (0.770 g, 4.65 mmol) was added and the mixture was heated to 130C under nitrogen for a further 3.5 h. The black oily solution was poured onto ice (200 g) and the aqueous solution was extracted with ethyl acetate (3 x 250 mL). The organic fractions were combined, removal of solvent in vacuo gave an oily solid which was triturated with ether. Filtration of the solid and washing with ether gave urethane (2) (88 mg, 9%) as a solid. APCI-MS Found [M + H] + = 241,243.
  • 3
  • [ 5305-59-9 ]
  • [ 628692-15-9 ]
  • [ 1192814-36-0 ]
YieldReaction ConditionsOperation in experiment
51% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 125℃; for 0.333333h;Microwave irradiation; Step A: 2'-methoxy-4,5'-bipyrimidin-6-amine6-Chloropyrimidin-4-amine (0.35 g, 2.70 mmol), 2-methoxypyrimidin-5- ylboronic acid (0.520 g, 3.38 mmol), Na2C03 (0.859 g, 8.11 mmol) andbis(triphenylphosphine)palladium(II) chloride (0.038 g, 0.054 mmol) were suspended in a mixture of DME/EtOH/water. (15:2:3 mL). The mixture was heated in the microwave synthesizer at 125 °C for 20 min and concentrated. The residue was purified by silica gel chromatography (0-5 percent 9: 1 methanol: ammonium hydroxide- ethyl acetate) to afford 6-(pyridin-3-yl)pyrimidin-4-amine (0.28 g, 1.378 mmol, 51 percent yield) as an off-white solid. LCMS R.T. = 0.53; [M+H]+ = 204.11.
51% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 125℃; for 0.333333h;Microwave irradiation; 6-Chloropyrimidin-4-amine (0.35 g, 2.70 mmol),<strong>[628692-15-9]2-methoxypyrimidin-5-ylboronic acid</strong> (0.520 g, 3.38 mmol),Na2CO3 (0.859 g, 8.11 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.038 g, 0.054 mmol) were suspendedin a mixture of DME/EtOH/water. (15:2:3 mL). Themixture was heated in the microwave synthesizer at 125° C.for 20 min and concentrated. The residue was purified bysilica gel chromatography (0-5percent 9:1 methanol:ammoniumhydroxide-ethyl acetate) to afford 6-(pyridin-3-yl)pyrimidin4-amine (0.28 g, 1.378 mmol, 51percent yield) as an off-white solid.
  • 4
  • [ 261953-36-0 ]
  • [ 5305-59-9 ]
  • [ 1394120-84-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In N,N-dimethyl-formamide; oil; at 0 - 70℃; for 23.1667h; Step 1-Synthesis of 6-(6-iodoindazol-1-yl)pyrimidin-4-amine To a solution of <strong>[261953-36-0]6-iodoindazole</strong> (500 mg, 2.05 mmol) in DMF (8 mL) was added NaH (60% oil dispersion, 131.12 mg, 3.28 mmol) at 0 C. The mixture was stirred at 0 C. to RT for 10 minutes before addition of 6-chloropyrimidin-4-amine (477.78 mg, 3.69 mmol) and stirring at 60 C. for 17 hr and then transferred to a pressure tube and heated at 70 C. for a further 6 hr. The reaction mixture was cooled and quenched by the addition of water (10 ml) and EtOAc (a few drops) was added. The resultant precipitate was collected by suction filtration and then thoroughly dried under high vacuum to give the title intermediate (248 mg): LC-MS: m/z=+338.20 (M+H)+.
  • 5
  • [ 5305-59-9 ]
  • [ 189882-33-5 ]
  • C12H8N6 [ No CAS ]
  • 6
  • [ 5305-59-9 ]
  • [ 35344-95-7 ]
  • 1-(6-aminopyrimidin-4-yl)-1H-imidazole-4-formaldehyde [ No CAS ]
  • 7
  • [ 5305-59-9 ]
  • [ 872-82-2 ]
  • 2-(1-(6-aminopyrimidin-4-yl)-1H-imidazole-4-yl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h; A solution of 1.12 g (10 mmol) of 2- (1 H-imidazol-4-yl) ethan-1-ol was dissolved in 20 ml of DMF, 1.30 g of (lOmmol) of 4-amino-6-chloroetine, g (12 mmol) of cesium carbonate, the temperature was raised to 140 C and the reaction was stirred for 12 h. And the residue was purified by silica gel column chromatography. The eluent was methanol: dichloromethane = 1: 30 to give 1.19 g of the compound as shown on the white solid (yield of the compound of the formula IIb-1) in a yield of 58%.
58% With caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h; General procedure: A mixture of imidazole derivatives (4a-c, 10mmol), 4-amino-6-chloropyrimidine (1.30g, 10mmol), and K2CO3 (2.07g, 15mmol, for 5a) or Cs2CO3 (3.91g, 12mmol, for 5b-c) was stirred in DMF (20mL) at 100C (for 5a) or at 140C (for 5b-c) for 12h. Water (100mL) was then added. The mixture was extracted with EtOAc (3×50mL). The organic layer was separated and dried over Na2SO4. Removal of the solvents produced a residue which was purified using column chromatography and eluted with a mixture of MeOH:CH2Cl2 (1:30, v:v) to afford 5a-c.
  • 8
  • [ 5305-59-9 ]
  • [ 6358-77-6 ]
  • C11H11BrN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: 4-amino-6-chloropyrimidine (200 mg, 1.54 mmol) and KI(127.82 mg, 0.77 mmol) was dissolved in ethanol (35 mL). Trifluoroaceticacid (200 mL) was added after stirring and heating10 min for activating pyrimidine. Then to a stirred solution ofsubstituted aniline (1.23 mmol) in ethanol (15 mL) was added byway of drip for 1 h. The resulting mixture was heated to reflux for36 h, allowed to cool to room temperature, and concentrated invacuo. Then the solid residue was diluted with ethyl acetate and asaturated aqueous solution of NaHCO3. The aqueous layer wasseparated and extracted with ethyl acetate. The organic phase waswashed with brine, dried (Na2SO4), filtered, and concentrated. Purificationof the crude product by silica gel column chromatography(ethyl acetate/light petroleum, 2:1 and 1:1), provided the desiredproduct (batch1). Substituted aniline (2,6-dichloro and 3,5-dimethoxy) (200 mg) was dissolved in CH2Cl2 (15 mL) was addedby way of drip phosgene which dissolved in CH2Cl2 (20 mL)(batch1/phosgene, 2:1 (mol)) at 0 C for 0.5 h. The resulting mixturewas heated to reflux for 3e6 h, allowed to cool to room temperature,and concentrated in vacuo. Then the solid residue was dilutedwith ethyl acetate and a saturated aqueous solution of NaHCO3. Theaqueous layer was separated and extracted with ethyl acetate. Theorganic phase was washed with brine, dried (Na2SO4), filtered, andconcentrated. Purification of the crude product by silica gel columnchromatography (CH2Cl2/MeOH/aqueous NH3, 96:3:1), providedthe desired product (batch2). Batch1 and batch2 (batch1/batch2,5:6 (mol)) were dissolved in toluene (10 mL,18.89 mmol), theresulting mixture was heated to reflux for 8e10 h, allowed to coolto room temperature, then filtered by toluene to provide the endproduct(the residue).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 5305-59-9 ]

Chlorides

Chemical Structure| 65766-32-7

A127168 [65766-32-7]

6-Chloro-N-methylpyrimidin-4-amine

Similarity: 0.91

Chemical Structure| 1749-68-4

A211484 [1749-68-4]

6-Chloro-2-methylpyrimidin-4-amine

Similarity: 0.88

Chemical Structure| 31058-83-0

A386147 [31058-83-0]

6-Chloro-N,N-dimethylpyrimidin-4-amine

Similarity: 0.86

Chemical Structure| 5767-35-1

A345220 [5767-35-1]

4-Chloro-6-hydrazinopyrimidine

Similarity: 0.86

Chemical Structure| 14394-56-0

A237075 [14394-56-0]

4-Amino-6-chloro-5-methylpyrimidine

Similarity: 0.84

Amines

Chemical Structure| 65766-32-7

A127168 [65766-32-7]

6-Chloro-N-methylpyrimidin-4-amine

Similarity: 0.91

Chemical Structure| 1749-68-4

A211484 [1749-68-4]

6-Chloro-2-methylpyrimidin-4-amine

Similarity: 0.88

Chemical Structure| 31058-83-0

A386147 [31058-83-0]

6-Chloro-N,N-dimethylpyrimidin-4-amine

Similarity: 0.86

Chemical Structure| 5767-35-1

A345220 [5767-35-1]

4-Chloro-6-hydrazinopyrimidine

Similarity: 0.86

Chemical Structure| 14394-56-0

A237075 [14394-56-0]

4-Amino-6-chloro-5-methylpyrimidine

Similarity: 0.84

Related Parent Nucleus of
[ 5305-59-9 ]

Pyrimidines

Chemical Structure| 65766-32-7

A127168 [65766-32-7]

6-Chloro-N-methylpyrimidin-4-amine

Similarity: 0.91

Chemical Structure| 1749-68-4

A211484 [1749-68-4]

6-Chloro-2-methylpyrimidin-4-amine

Similarity: 0.88

Chemical Structure| 31058-83-0

A386147 [31058-83-0]

6-Chloro-N,N-dimethylpyrimidin-4-amine

Similarity: 0.86

Chemical Structure| 5767-35-1

A345220 [5767-35-1]

4-Chloro-6-hydrazinopyrimidine

Similarity: 0.86

Chemical Structure| 14394-56-0

A237075 [14394-56-0]

4-Amino-6-chloro-5-methylpyrimidine

Similarity: 0.84