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[ CAS No. 58-14-0 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 58-14-0
Chemical Structure| 58-14-0
Structure of 58-14-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 58-14-0 ]

CAS No. :58-14-0 MDL No. :MFCD00057350
Formula : C12H13ClN4 Boiling Point : -
Linear Structure Formula :- InChI Key :WKSAUQYGYAYLPV-UHFFFAOYSA-N
M.W : 248.71 Pubchem ID :4993
Synonyms :
Pirimecidan;Pirimetamin;NSC 3061;Khloridin;Daraprim®;Darapram;RP 4753
Chemical Name :5-(4-Chlorophenyl)-6-ethylpyrimidine-2,4-diamine

Calculated chemistry of [ 58-14-0 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 71.06
TPSA : 77.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.69
Log Po/w (WLOGP) : 2.54
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 2.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.47
Solubility : 0.0848 mg/ml ; 0.000341 mol/l
Class : Soluble
Log S (Ali) : -3.98
Solubility : 0.0262 mg/ml ; 0.000105 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.87
Solubility : 0.00339 mg/ml ; 0.0000136 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.43

Safety of [ 58-14-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H351-H361 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58-14-0 ]

* 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 [ 58-14-0 ]

[ 58-14-0 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 105640-59-3 ]
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  • [ 106-31-0 ]
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  • [ 143947-38-0 ]
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  • [ 2082-59-9 ]
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  • [ 143947-39-1 ]
  • 6
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  • [ 108-24-7 ]
  • [ 74124-11-1 ]
  • [ 74124-12-2 ]
  • 7
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  • [ 108-24-7 ]
  • [ 74124-13-3 ]
  • 8
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  • [ 1538-75-6 ]
  • [ 143947-40-4 ]
  • 9
  • [ 58-14-0 ]
  • [ 123-62-6 ]
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  • 10
  • [ 58-14-0 ]
  • [ 93-97-0 ]
  • [ 143947-41-5 ]
  • 11
  • [ 58-14-0 ]
  • [ 75-36-5 ]
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  • 12
  • [ 58-14-0 ]
  • [ 91396-20-2 ]
  • [ 93456-61-2 ]
  • 13
  • [ 58-14-0 ]
  • [ 104498-88-6 ]
  • [ 93456-61-2 ]
  • 14
  • [ 58-14-0 ]
  • [ 21813-35-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid; Step A Synthesis of 2,4-diamino-6-ethyl-5-(4-chloro-3-nitrophenyl)pyrimidine as an intermediate (Compound 71) Concentrated sulfuric acid, 90 mL, and 70% nitric acid, 90 mL, were stirred together during which time the mixture warmed to about 65 C. The mixture was allowed to cool to about 50 C., and 30.0 grams (0.12 mole) of 2,4-diamino-6-ethyl-5-(4-chlorophenyl)pyrimidine (commercially available) was added portionwise during a 45 minute period, while maintaining the reaction mixture temperature at about 50-53 C. Upon completion of addition, the reaction mixture was stirred for one hour, while still maintaining the reaction mixture temperature at about 50 C. After this time, the reaction mixture was cooled and poured into ice. The resultant mixture was cooled further and, with stirring, was made basic with concentrated ammonium hydroxide. A precipitate was collected by filtration, rinsed with water and dried, yielding 35.4 grams of 2,4-diamino-6-ethyl-5-(4-chloro-3-nitrophenyl)pyrimidine, mp 220-223 C., dec. The NMR spectrum was consistent with the proposed structure.
  • 15
  • [ 58-14-0 ]
  • Phenoxy-acetic acid (E)-10-oxo-dec-5-enyl ester [ No CAS ]
  • 16
  • [ 58-14-0 ]
  • 4-amino-6-ethyl-1,3,5-triazin-2-yl p-chlorophenyl ketone [ No CAS ]
  • 17
  • [ 58-14-0 ]
  • 2-amino-5-(p-chlorophenyl)-t-6-ethyl-5,6-dihydro-r-5-hydroxy-4(3H)-pyrimidinone [ No CAS ]
  • 19
  • C12H12ClN6(1+)*BF4(1-) [ No CAS ]
  • [ 58-14-0 ]
  • 23
  • 1-(4-chlorophenyl)-1-cyano-2-methoxybut-1-ene [ No CAS ]
  • [ 50-01-1 ]
  • [ 58-14-0 ]
  • 24
  • [ 5734-66-7 ]
  • [ 58-14-0 ]
  • 25
  • [ 514854-12-7 ]
  • [ 58-14-0 ]
  • 26
  • [ 5734-67-8 ]
  • [ 58-14-0 ]
  • 29
  • [ 58-14-0 ]
  • C23H22BClN4O5 [ No CAS ]
  • 30
  • [ 58-14-0 ]
  • [ 344425-79-2 ]
  • 53
  • [ 58-14-0 ]
  • 5-(3-acetylmino-4-chlorophenyl)-2,4-diamino-6-ethylpyrimidine acetyl derivative [ No CAS ]
  • 55
  • [ 58-14-0 ]
  • 2,4-diamino-5-(5-azido-4-chloro-2-trifluoromethylsulphonyloxy)-6-ethylpyrimidine [ No CAS ]
  • 57
  • [ 58-14-0 ]
  • 2,4-diamino-5-(3-azido-4-chlorophenyl)-6-ethylpyrimidine ethanesulphonic acid salt [ No CAS ]
  • 59
  • [ 58-14-0 ]
  • 2,4-diamino-5-(4-azido-3-methoxyphenyl)-6-ethylpyrimidine ethanesulphonate [ No CAS ]
  • 60
  • [ 58-14-0 ]
  • 2,4-diamino-5-(4-azido-3-ethoxyphenyl)-6-ethylpyrimidine ethylsulphonate [ No CAS ]
  • 61
  • [ 58-14-0 ]
  • 2,4-diamino-5-(3-amino-4-chlorophenyl)-6-ethylpyrimidine diethanesulphonic acid salt [ No CAS ]
  • 69
  • 2,4-diamino-5-<4-chloro-3-(3-methyltriazen-1-yl)phenyl>-6-ethylpyrimidine [ No CAS ]
  • [ 58-14-0 ]
  • 79
  • [ 100709-69-1 ]
  • [ 58-14-0 ]
  • 80
  • [ 1336-21-6 ]
  • [ 58-14-0 ]
  • [ 21813-35-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid; Step A Synthesis of 2,4-diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine as an intermediate A stirred solution of 75 mL of 70% nitric acid and 75 mL of concentrated sulfuric acid warmed to about 50 C. from the heat of solution. To this was added 25 grams (0.10 mole) of 2,4-diamino-5-(4-chloro-phenyl)-6-ethylpyrimidine (commercially available) during a 10 minute period. Upon completion of addition, the reaction mixture was stirred at 50 C. for about 1 hour. After this time, the reaction mixture was allowed to cool to ambient temperature where it was stirred for about 18 hours. The reaction mixture was then poured into 1000 mL of ice containing 110 mL of concentrated ammonium hydroxide. The resultant solid was collected by filtration and recrystallized from aqueous ethanol, yielding 29.2 grams of 2,4-diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine. The NMR spectrum was consistent with the proposed structure.
  • 81
  • [ 58-14-0 ]
  • nitropyrimethamine [ No CAS ]
  • [ 21813-35-4 ]
YieldReaction ConditionsOperation in experiment
93.8% a) 2,4,-Diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine 2,4,-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine (103.8 g, 0.417 mol) ("Pyrimethamine" obtained from Sigma Chemical Co. Ltd.) was added in portions to a stirred mixture of concentrated nitric acid (210 ml) and concentrated sulphuric acid (210 ml). The mixture was heated at 50 C. for 1 h and then set aside at room temperature for 2.5 days. The reaction mixture was poured onto concentrated ammonia ("0.88" 5 dm3)/ice to effect a neutralisation. The resulting precipitate was collected by filtration and washed with water and sucked to dryness to give nitropyrimethamine as a yellow solid (115 g, 93.8% yield).
  • 82
  • [ 917499-87-7 ]
  • [ 58-14-0 ]
  • Rh2(O2CCH3)4((NH2)2C4(C2H5)N2C6H4Cl)2 [ No CAS ]
  • 83
  • [ 100-21-0 ]
  • [ 58-14-0 ]
  • pyrimethaminium terephthalate [ No CAS ]
  • 84
  • [ 58-14-0 ]
  • bis(pyrimethamine) hexafluorosilicate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen fluoride; silica gel; In methanol; water;Heating; Compounds 1 and 2 were prepared by adding a slightly excess quantity of aqueous hydrofluoric acid (HF) to a hot methanolic solution of thiabendazole (Merck, Sharp & Dohme Inc., USA) or pyrimethamine (Lupin Laboratories Ltd., India) taken in a glass beaker (hydrofluorosilicic acid was produced in situ by the reaction of HF with silica of glass). The solutions were allowed to cool to room temperature. Within few hours, colourless crystals were obtained.
  • 85
  • [ 123-99-9 ]
  • [ 58-14-0 ]
  • C9H16O4*C12H13ClN4 [ No CAS ]
  • 86
  • [ 124-04-9 ]
  • [ 58-14-0 ]
  • [ 1043448-70-9 ]
  • 87
  • [ 111-16-0 ]
  • [ 58-14-0 ]
  • [ 1391742-71-4 ]
  • 88
  • [ 505-48-6 ]
  • [ 58-14-0 ]
  • C8H14O4*C12H13ClN4 [ No CAS ]
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