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[ CAS No. 24332-20-5 ] {[proInfo.proName]}

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Chemical Structure| 24332-20-5
Chemical Structure| 24332-20-5
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Product Details of [ 24332-20-5 ]

CAS No. :24332-20-5 MDL No. :MFCD00008486
Formula : C5H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :DYOZNCVZPFIXLU-UHFFFAOYSA-N
M.W : 120.15 Pubchem ID :47520
Synonyms :

Calculated chemistry of [ 24332-20-5 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.4
TPSA : 27.69 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) : -7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : -0.05
Log Po/w (WLOGP) : 0.25
Log Po/w (MLOGP) : -0.25
Log Po/w (SILICOS-IT) : 0.16
Consensus Log Po/w : 0.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.29
Solubility : 61.7 mg/ml ; 0.514 mol/l
Class : Very soluble
Log S (Ali) : -0.08
Solubility : 99.7 mg/ml ; 0.83 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.67
Solubility : 25.9 mg/ml ; 0.215 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 24332-20-5 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:3271
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24332-20-5 ]

* 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 [ 24332-20-5 ]
  • Downstream synthetic route of [ 24332-20-5 ]

[ 24332-20-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 506-93-4 ]
  • [ 68-12-2 ]
  • [ 24332-20-5 ]
  • [ 13418-77-4 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: at 20 - 60℃; for 1.25 h;
Stage #2: at 70℃; for 0.75 h;
Stage #3: With sodium hydroxide In methanol at 0 - 100℃; for 1.75 h;
a) 5-Methoxypyrimidin-2-amine (I-22). [0207] Phosphorus pentachloride (8.07 g; 38.78 mmol; 1 eq) was added portion-wise to methoxyacetaldehyde dimethyl acetal (5 mL; 38.78 mmol; 1 eq) kept at 20°C. The reaction mixture was heated at 60°C for 1 hour and 15 minutes, then cooled down to 0°C, before adding anhydrous dimethylformamide (9 mL; 116.3 mmol; 3 eq) dropwise. The reaction mixture was heated at 70°C for 45 minutes, then cooled at 0°C before adding methanol (40 mL) followed by sodium hydroxide (20.1 g; 504 mmol; 13 eq) and guanidine nitrate (9.46 g; 77.56 mmol; 2 eq). The reaction mixture was stirred at 0°C for 15 minutes. The reaction mixture was allowed to reach at room temperature and methanol was evaporated. The resulting solution was heated at 100°C for 1 hour and 30 minutes. Water (200 mL) and ice was added and the aqueous layer was extracted with dichloromethane (3 x 250 mL). The combined organic layers were washed with saturated sodium chloride (150 mL), dried over sodium sulfate, filtered and concentrated to dryness. The title compound 5-methoxypyrimidin-2-amine was obtained in 53 percent yield (2.6 g) as a brown solid. 1H-NMR (DMSO-d6): δ (ppm) 3.73 (s, 3H), 6.16 (s, 2H), 8.04 (s, 2H).
53%
Stage #1: at 20 - 60℃; for 1.25 h;
Stage #2: at 0 - 70℃; for 0.75 h;
Stage #3: With sodium hydroxide In methanol at 0 - 100℃; for 1.75 h;
a) 5-Methoxypyrimidin-2-amine (1-22). NaOH, MeOH Phosphorus pentachloride (8.07 g; 38.78 mmol; 1 eq) was added portion-wise to methoxyacetaldehyde dimethyl acetal (5 mL; 38.78 mmol; 1 eq) kept at 20°C. The reaction mixture was heated at 60°C for 1 hour and 15 minutes, then cooled down to 0°C, before adding anhydrous dimethylformamide (9 mL; 116.3 mmol; 3 eq) dropwise. The reaction mixture was heated at 70°C for 45 minutes, then cooled at 0°C before adding methanol (40 mL) followed by sodium hydroxide (20.1 g; 504 mmol; 13 eq) and guanidine nitrate (9.46 g; 77.56 mmol; 2 eq). The reaction mixture was stirred at 0°C for 15 minutes. The reaction mixture was allowed to reach at room temperature and methanol was evaporated. The resulting solution was heated at 100°C for 1 hour and 30 minutes. Water (200 mL) and ice was added and the aqueous layer was extracted with dichloromethane (3 x 250 mL). The combined organic layers were washed with saturated sodium chloride (150 mL), dried over sodium sulfate, filtered and concentrated to dryness. The title compound 5- methoxypyrimidin-2-amine was obtained in 53percent yield (2.6 g) as a brown solid. 1H- NMR (DMSO-d6): δ (ppm) 3.73 (s, 3H), 6.16 (s, 2H) , 8.04 (s, 2H).
20%
Stage #1: at 30 - 60℃; for 1.25 h;
Stage #2: at 0 - 70℃; for 1.25 h;
Stage #3: With sodium hydroxide In methanol at 20 - 40℃; for 0.25 h;
Step 1:
PCl5 (42.0 g, 200 mmol) was added in portions to 1,1,2-trimethoxyethane (25.2 mL, 200 mmol) maintained below 30° C.
The mixture was then heated to 60° C. for 75 minutes followed by cooling to 0° C. 45 mL of DMF (600 mmol) was drop-wise added and the mixture was stirred at room temperature for 30 minutes, followed by stirring for 45 minutes at 70° C.
After cooling, 200 mL of MeOH was added at 0° C., followed by NaOH (60 g, 2.6 mol) and guanidine nitrate (48 g, 400 mmol) below 40° C.
After stirring at room temperature for 15 minutes, MeOH was removed under vacuum, and the residue was heated at 100° C. for 1 hour.
The mixture was then poured onto ice, exacted with CHCl3, dried over Na2SO4 and filtered.
Solvent evaporation gave a brown oil, which after CC with EtOAc gave 5.02 g (20percent) of yellow solid 5-methoxy-2-aminopyrimidine.
The structure was confirmed by 1H-NMR and EI-MS. EI-MS (m/z) 125 (M+).
Reference: [1] Patent: EP2664616, 2013, A1, . Location in patent: Paragraph 0207-0208
[2] Patent: WO2013/171281, 2013, A1, . Location in patent: Page/Page column 109-110
[3] Patent: US2009/105269, 2009, A1, . Location in patent: Page/Page column 10
  • 2
  • [ 67-56-1 ]
  • [ 9004-34-6 ]
  • [ 1917-64-2 ]
  • [ 13984-50-4 ]
  • [ 24332-20-5 ]
Reference: [1] Green Chemistry, 2015, vol. 17, # 7, p. 4037 - 4044
  • 3
  • [ 67-56-1 ]
  • [ 110-71-4 ]
  • [ 24332-20-5 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 24, p. 5797 - 5806
  • 4
  • [ 67-56-1 ]
  • [ 9004-34-6 ]
  • [ 96-35-5 ]
  • [ 547-64-8 ]
  • [ 24332-20-5 ]
Reference: [1] ChemSusChem, 2017, vol. 10, # 7, p. 1390 - 1394
  • 5
  • [ 57-50-1 ]
  • [ 109-87-5 ]
  • [ 547-64-8 ]
  • [ 107-31-3 ]
  • [ 79-20-9 ]
  • [ 624-45-3 ]
  • [ 24332-20-5 ]
Reference: [1] Catalysis Communications, 2014, vol. 49, p. 78 - 81
  • 6
  • [ 7252-83-7 ]
  • [ 124-41-4 ]
  • [ 24332-20-5 ]
Reference: [1] Chemische Berichte, 1930, vol. 63, p. 422 Anm.14
[2] Organic Letters, 2007, vol. 9, # 20, p. 4061 - 4063
  • 7
  • [ 67-56-1 ]
  • [ 107-25-5 ]
  • [ 24332-20-5 ]
Reference: [1] Canadian Journal of Chemistry, 1969, vol. 47, p. 2117 - 2118
  • 8
  • [ 67-56-1 ]
  • [ 7252-83-7 ]
  • [ 24332-20-5 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1961, p. 1570 - 1572[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1961, p. 1685 - 1688
  • 9
  • [ 68-12-2 ]
  • [ 24332-20-5 ]
  • [ 14884-01-6 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: at 0 - 20℃; for 0.5 h;
Stage #2: at 0 - 55℃; for 1 h;
Stage #3: With hydrazine hydrate In ethanol for 3 h; Inert atmosphere
To 1,1,2-trimethoxyethane (300 mmol, 1.0 equiv.) at 0°C with stirring was added phosphorus pentachloride (300 mmol, 1.0 equiv.) portion-wise (temperature was kept below 20°C). The mixture was stirred for 30 minutes at ambient temperature and re-cooled to 0°C. Anhydrous DMF (880 mmol, 2.9 equiv.) was added dropwise via addition funnel (temperature was kept below 20°C) and the mixture was slowly warmed to 55 °C () as a light amber solid
Reference: [1] Patent: WO2016/44446, 2016, A2, . Location in patent: Paragraph 00449; 000450
  • 10
  • [ 68-12-2 ]
  • [ 24332-20-5 ]
  • [ 13616-34-7 ]
Reference: [1] Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1967, vol. 300, p. 704 - 708
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