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[ CAS No. 4558-59-2 ] {[proInfo.proName]}

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Chemical Structure| 4558-59-2
Chemical Structure| 4558-59-2
Structure of 4558-59-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4558-59-2 ]

CAS No. :4558-59-2 MDL No. :MFCD01912557
Formula : C7H8N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WQGFZQFGVYDFOP-UHFFFAOYSA-N
M.W : 168.15 Pubchem ID :4436645
Synonyms :

Calculated chemistry of [ 4558-59-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.4
TPSA : 61.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 0.27
Log Po/w (WLOGP) : 0.31
Log Po/w (MLOGP) : -0.68
Log Po/w (SILICOS-IT) : 0.99
Consensus Log Po/w : 0.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.22
Solubility : 10.0 mg/ml ; 0.0596 mol/l
Class : Very soluble
Log S (Ali) : -1.12
Solubility : 12.8 mg/ml ; 0.0761 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.85
Solubility : 2.38 mg/ml ; 0.0141 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 4558-59-2 ]

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

Application In Synthesis of [ 4558-59-2 ]

* 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 [ 4558-59-2 ]
  • Downstream synthetic route of [ 4558-59-2 ]

[ 4558-59-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 5305-40-8 ]
  • [ 4558-59-2 ]
YieldReaction ConditionsOperation in experiment
46.3% at 90℃; for 1 h; The compound 4,6-dichloropyrimidine-5-carbaldehyde (5 g, 28.25 mmol) was suspended in dry MeOH (100 mL)After K2CO3 (7.8 g, 56.5 mmol) was added thereto, the reaction mixture was stirred at 90 ° C for 1 hour and then concentrated under reduced pressure to giveThe residue was dissolved in a mixed solvent of water (100 mL) and DCM (100 mL), separated on a liquid phase, the aqueous phase was extracted with DCM (50 mL × 3)The combined organic phases were concentrated under reduced pressure, the residue was diluted in DCM / PE (1 mL / 20 mL) and the resulting mixture stirred at room temperatureThe mixture was stirred for 3 hours and then filtered off with suction to give a yellow solid which was purified by silica gel column chromatography (PE / EtOAc (v / v) = 5/1)Purification gave the title compound as a white solid (2.2 g, 46.3percent).
Reference: [1] Patent: CN104513235, 2017, B, . Location in patent: Paragraph 1355; 1356; 1357; 1384; 1385; 1386
  • 2
  • [ 5305-40-8 ]
  • [ 77-92-9 ]
  • [ 4558-59-2 ]
YieldReaction ConditionsOperation in experiment
20% With sodium methylate In methanol REFERENCE EXAMPLE 15
Preparation of 4,6-dimethoxypyrimidine-5-carboaldehyde
43.6g (246 mmol) of 4,6-dichloropyrimidine-5-carboaldehyde was dissolved in 200 m of methanol, and 120g (622 mmol) of 28percent sodium methoxide was added under cooling with ice and then reacted for 2 hours at room temperature.
After completion of the reaction, the solvent was distilled off, and an aqueous citric acid solution was added, followed by extraction with ethyl acetate.
The organic layer was washed with an aqueous sodium hydrogencarbonate solution, an aqueous citric acid solution, water and an aqueous sodium chloride solution in this order, dried and concentrated, and the obtained crude crystals were washed with isopropyl ether to obtain 8.3g (yield: 20percent) of 4,6-dimethoxypyrimidine-5-carboaldehyde.
Reference: [1] Patent: EP1211246, 2002, A1,
  • 3
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 5305-40-8 ]
  • [ 4558-59-2 ]
YieldReaction ConditionsOperation in experiment
44% at 0 - 70℃; for 2 h; The compound 4,6-dichloropyrimidine-5-carbaldehyde (20 g, 113.0 mmol) was suspended in dry methanol (100 mL)To the reaction was slowly added a solution of sodium methoxide (27.47 g, 508.5 mmol) in dry methanol (100 mL) at 0 ° C. The reaction was warmed to 70 ° C and stirred for 2 hours, then cooled to 0 ° C and quenched by the addition of aqueous hydrochloric acid (1M, 300 mL). The resulting mixture was neutralized to pH = 7 by the addition of saturated aqueous NaHCO 3 and the mixture was washed with The residue was purified by silica gel column chromatography (diethyl ether / ethyl acetate = 4/1) The title compound was obtained as a white solid (8.37 g, 44percent).
Reference: [1] Patent: CN104513235, 2017, B, . Location in patent: Paragraph 0781; 0782; 0783
  • 4
  • [ 3315-60-4 ]
  • [ 5305-40-8 ]
  • [ 4558-59-2 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 42, p. 7545 - 7548
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