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[ CAS No. 13566-71-7 ] {[proInfo.proName]}

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Chemical Structure| 13566-71-7
Chemical Structure| 13566-71-7
Structure of 13566-71-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13566-71-7 ]

CAS No. :13566-71-7 MDL No. :MFCD00234623
Formula : C10H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WTDXDRUHQKVYKO-UHFFFAOYSA-N
M.W :188.18 Pubchem ID :241011
Synonyms :

Calculated chemistry of [ 13566-71-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.51
TPSA : 66.24 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : 1.2
Log Po/w (SILICOS-IT) : 1.49
Consensus Log Po/w : 1.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.206 mg/ml ; 0.00109 mol/l
Class : Soluble
Log S (Ali) : -3.23
Solubility : 0.112 mg/ml ; 0.000595 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.179 mg/ml ; 0.000953 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 13566-71-7 ]

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

Application In Synthesis of [ 13566-71-7 ]

* 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 [ 13566-71-7 ]
  • Downstream synthetic route of [ 13566-71-7 ]

[ 13566-71-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 13566-71-7 ]
  • [ 3740-92-9 ]
YieldReaction ConditionsOperation in experiment
84% at 100℃; for 48 h; Green chemistry General procedure: To 40 g of the 2-substituted 6-hydroxy-[3H]-pyrimidin-4-one 4, 300 mL of phosphoryl chloride was added. The mixture was heated for 48 h at 100°C. The excess of phosphoryl chloride was removed by distillation under reduced pressure (20 mbar). Chloroform (200 mL) and ice water (100 mL) were added and the mixture was well stirred for 30 min. The solution was adjusted to pH 5–6 with aqueous sodium carbonate solution. The organic layer was separated and the water phase was extracted three times with 200 mL of chloroform. The combined chloroform phases were dried with magnesium sulfate, filtered, and finally the chloroform was removed under reduced pressure. The obtained crude material was distilled under reduced pressure or purified by column chromatography using silica gel, mesh 60, and chloroform.
71%
Stage #1: for 12 - 16 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In water
A mixture of compound 2-phenyl-pyrimidlne-4,6-diol (33 g, 175.5 mmol) andPOCl3 (300 ml) was refluxed for 12-16 hours, excess Of POCl3 was distilled out and the crude was neutralized by saturated sodiumbicarbonte solution. The solid obtained was filtered and dried under vacuum to afford the compound 4,6-dichloro-2-phenyl- pyrimidine (28 g, 71percent) as off white solid.
62% for 3 h; Heating / reflux Example 6; Step a: 4,6-Dichloro-2-phenyl-pyrimidine (6a); To a mixture of 2-phenylpyrimidine-4,6-diol (7 g, 0.037 mol) in POCI3 (26 ml,0.279 mol), amine was added slowly (11.8 ml, 0.074 mol). The reaction mixture was heated to reflux for 3h. Some of the POCI3 was evaporated, and the residue was poured on ice followed by extraction with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated to give the title compound (5.16 g, 62percent), MS (M+H)+226.
Reference: [1] Patent: US2003/162764, 2003, A1,
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2627 - 2634
[3] Patent: US6372751, 2002, B1, . Location in patent: Example Pr3
[4] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
[5] Farmaco, 1997, vol. 52, # 1, p. 61 - 65
[6] Patent: WO2006/34473, 2006, A2, . Location in patent: Page/Page column 249-250
[7] Patent: WO2008/95999, 2008, A1, . Location in patent: Page/Page column 74
[8] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 2629 - 2634
  • 2
  • [ 13566-71-7 ]
  • [ 3740-92-9 ]
YieldReaction ConditionsOperation in experiment
86.06% at 110℃; for 3 h; The intermediate (1.75 g, 9.30 mmol) was added to a 100 mL round-bottomed flask, and phosphorus oxychloride (3.57 g, 23.23 mmol) in an oil bath at 110 ° C and the progress of the reaction was checked by thin layer chromatography.3 h after the end of the reaction, careful drop of ice water until precipitation precipitation is no longer so far,The reaction mixture, which had been cooled to room temperature, was filtered under reduced pressure, and the resulting precipitated crude product was purified by recrystallization from ethanol to give a pale yellow solid 5 (1.79 g, yield 86.06percent).
Reference: [1] Patent: CN106188014, 2016, A, . Location in patent: Paragraph 0017
  • 3
  • [ 108-59-8 ]
  • [ 13566-71-7 ]
YieldReaction ConditionsOperation in experiment
80% With sodium methylate; sodium chloride In methanol at 55℃; for 2 h; Example 69[0299] Benzamidine hydrochloride (26.0 gm, 0.166 moles) and dimethyl malonate (21.9 gm, 0.166 moles) were combined in dry methanol (200 mL). This mixture was stirred as 30percent sodium methoxide in methanol (89.7 gm, 0.498 moles) was added. A precipitate of sodium chloride formed and this mixture was stirred at 55°C. for 2 hours. The reaction mixture was diluted with water (500 mL) to form a clear solution. This was acidified by the addition of acetic acid (35 mL) causing a white precipitate to quickly form. After stirring for 30 minutes, the solid was isolated by filtration. The filter cake was washed, in turn with water, methanol and acetone. After drying, the 2-phenyl-4,6-dihydroxypyrimidine was obtained in a yield of 25 gm (80percent)) as a white solid.
Reference: [1] Patent: WO2012/167046, 2012, A1, . Location in patent: Page/Page column 134
  • 4
  • [ 1670-14-0 ]
  • [ 108-59-8 ]
  • [ 13566-71-7 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With sodium methylate In methanol at 55℃; for 2 h;
Stage #2: With acetic acid In methanol; water for 0.5 h;
Benzamidine hydrochloride (26.0 gm, 0.166 moles) and dimethyl malonate (21.9 gm, 0.166 moles) were combined in dry methanol (200 mL). This mixture was stirred as 30percent sodium methoxide in methanol (89.7 gm, 0.498 moles) was added. A precipitate of sodium chloride formed and this mixture was stirred at 55°C. for 2 hours. The reaction mixture was diluted with water (500 mL) to form a clear solution. This was acidified by the addition of acetic acid (35 mL) causing a white precipitate to quickly form. After stirring for 30 minutes, the solid was isolated by filtration. The filter cake was washed, in turn with water, methanol and acetone. After drying, the 2-phenyl-4,6-dihydroxypyrimidine was obtained in a yield of 25 gm (80percent) as a white solid.
Reference: [1] Patent: WO2012/167053, 2012, A1, . Location in patent: Page/Page column 92
  • 5
  • [ 1670-14-0 ]
  • [ 105-53-3 ]
  • [ 13566-71-7 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: for 16 h; Heating / reflux
Example 113Synthesis of(6-morpholm-4-yl-2-phenyl-pyrimidin-4-yl)-(4-trifltιorσmethoxy-phenyl)- amineStep (i). Synthesis of 2-phenyl-pyrimidine-4, 6-diol Sodium ethoxide was generated in-situ by adding sodium (18.4 g, 801 mmol) to absolute ethanol (500 mL) and then benazamidine hydrochloride (50 g, 320 mmol) was added followed by diethylmalonate (48.8 mL, 320 mmol), This reaction mixture was allowed to stir at refluxing temperature for 16 hours, under nitrogen atmosphere. Then the mixture was cooled to room temperature and concentrated tinder reduced pressure. The crude white solid was dissolved in water, acidified with 2N HCl. White solid obtained was filtered off, washed with z-propanol and dried to afford the compound 2-phenyl-pyrimidine-4,6-diol (34 g, 56percent) as off white solid.; Example 174Synthesis of 2-phenyl-pyrimidine-4, 6-diol This compound was prepared by a procedure analogous to that disclosed in Example 113 (step i), using starting materials with the appropriate substitution.
145 g With sodium ethanolate In ethanol for 4 h; Reflux; Green chemistry General procedure: Dry hydrogen chloride (1.3 mol) was added to an ice-cooled solution of 1 mol nitrile and 1.3 mol ethanol. The solution was stirred for two days at room temperature. A solution of 25 g (1.5 mol) of ammonia in absolute ethanol was prepared and added to the formed imido acid ethyl ester solution. The reaction mixture was stirred for 5 h, the precipitated NH4Cl was filtered off, and the clear solution was stored in a closed flask. A sodium ethanolate solution was prepared with 46 g (2 mol) of sodium in1 L of ethanol. The amidine hydrochloride–ethanol solution and 160 g (1 mol) of diethyl malonate were added. A white precipitate was immediately formed and the mixture was refluxed for 4 h. The solvent was distilled off under reduced pressure, and the crude sodium salt was dissolved in 1 L of water. From the clear solution the 2-substituted 6-hydroxy-[3H]-pyrimidin-4-one was precipitated by addition of aqueous concentrated hydrochloric acid. The precipitate was isolated, washed with distilled water, and dried under vacuum at 80°C for 6 h.
Reference: [1] Farmaco, 1997, vol. 52, # 1, p. 61 - 65
[2] Patent: WO2006/34473, 2006, A2, . Location in patent: Page/Page column 249; 292
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2627 - 2634
[4] Patent: US6372751, 2002, B1, . Location in patent: Example Pr1
[5] Patent: US2003/162764, 2003, A1,
[6] Patent: US6372740, 2002, B1,
[7] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
  • 6
  • [ 618-39-3 ]
  • [ 108-59-8 ]
  • [ 13566-71-7 ]
Reference: [1] Patent: US5216159, 1993, A,
[2] Patent: US5326868, 1994, A,
  • 7
  • [ 152335-99-4 ]
  • [ 108-59-8 ]
  • [ 13566-71-7 ]
Reference: [1] Patent: US5597920, 1997, A,
  • 8
  • [ 5333-86-8 ]
  • [ 13566-71-7 ]
Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
  • 9
  • [ 100-47-0 ]
  • [ 13566-71-7 ]
Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
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