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[ CAS No. 6214-64-8 ] {[proInfo.proName]}

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Chemical Structure| 6214-64-8
Chemical Structure| 6214-64-8
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Product Details of [ 6214-64-8 ]

CAS No. :6214-64-8 MDL No. :MFCD01875049
Formula : C8H10N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :UNZAXNKEIQRZBJ-UHFFFAOYSA-N
M.W : 182.18 Pubchem ID :665021
Synonyms :

Calculated chemistry of [ 6214-64-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.11
TPSA : 72.31 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : 0.67
Log Po/w (MLOGP) : 0.06
Log Po/w (SILICOS-IT) : 1.02
Consensus Log Po/w : 0.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.62
Solubility : 4.4 mg/ml ; 0.0242 mol/l
Class : Very soluble
Log S (Ali) : -1.9
Solubility : 2.29 mg/ml ; 0.0126 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.95
Solubility : 2.06 mg/ml ; 0.0113 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 6214-64-8 ]

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 [ 6214-64-8 ]

* 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 [ 6214-64-8 ]
  • Downstream synthetic route of [ 6214-64-8 ]

[ 6214-64-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 6319-01-3 ]
  • [ 6214-65-9 ]
  • [ 6214-64-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1994, vol. 59, # 8, p. 1841 - 1852
[2] Collection of Czechoslovak Chemical Communications, 1994, vol. 59, # 8, p. 1841 - 1852
  • 2
  • [ 6214-64-8 ]
  • [ 188781-08-0 ]
YieldReaction ConditionsOperation in experiment
85% at 105℃; for 0.5 h; General procedure: A solution of compound 2 (10 mmol) in phosphorous oxychloride (10 mL) was heated under reflux for 30 min. The resulting reaction mixture was distilled under reduced pressure to remove excess phosphorous oxychloride. Last traces of phosphorous oxychloride were removed by azeotrophic distillation with dry benzene and crude product was purified by column chromatography to afford pure product 3.
13.18% at 80℃; for 12 h; Inert atmosphere To a solution of ethyl 6-methyl-2-oxo-1 2-dihydropyrimidine-5-carboxylate (62 g 340 mmol) stirred under N2 at 20 was added POCl3 (496 g 3233 mmol) slowly. The reaction mixture was stirred at 80 for 12 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine dried over Na2SO4 filtered and concentrated. The residue was purified by silica column chromatography (PE/EA 101) . All fractions found to contain product by TLC (PE/EA 101 Rf 0.7) were combined and concentrated to yield a yellow solid of ethyl 2-chloro-4-methylpyrimidine-5-carboxylate (9 g 44.9 mmol 13.18yield) 1H NMR (400 MHz CDCl3) δ 9.01 (s 1H) 4.41 (q J 7.2 Hz 2H) 2.82 (s 3H) 1.41 (t J 7.2 Hz 3H) .
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2290 - 2294
[2] Patent: WO2016/37578, 2016, A1, . Location in patent: Page/Page column 70
[3] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 314 - 323
  • 3
  • [ 6214-64-8 ]
  • [ 188781-08-0 ]
YieldReaction ConditionsOperation in experiment
45% for 2 h; Reflux A mixture of POCI3 (10ml) and 2-hydroxy-4-methyl-pyrimidine-5-carboxylic acid ethyl ester (Frontier, lg, 5.49mmol) was heated to reflux for 2h. Excess POCI3 and diethyl iso-propylamine were removed by evaporation under vacuum. The residue was partitioned between 10percent NaOH and EtOAc. The organic extract was washed with water and brine, dried over Na2S04, filtered and concentrated to give the desired product (498mg, 45percent yield).
Reference: [1] Patent: WO2012/123467, 2012, A1, . Location in patent: Page/Page column 30
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 18, p. 2573 - 2577
[3] Patent: US5935966, 1999, A,
[4] Patent: US5811428, 1998, A,
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