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[ CAS No. 2239-83-0 ] {[proInfo.proName]}

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Chemical Structure| 2239-83-0
Chemical Structure| 2239-83-0
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Product Details of [ 2239-83-0 ]

CAS No. :2239-83-0 MDL No. :MFCD09414732
Formula : C6H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :HOBMGFDJYBEWLS-UHFFFAOYSA-N
M.W : 124.14 Pubchem ID :14686706
Synonyms :

Calculated chemistry of [ 2239-83-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.13
TPSA : 46.01 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) : -7.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : -0.28
Log Po/w (WLOGP) : 0.13
Log Po/w (MLOGP) : -0.61
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 0.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.86
Solubility : 17.1 mg/ml ; 0.138 mol/l
Class : Very soluble
Log S (Ali) : -0.23
Solubility : 73.6 mg/ml ; 0.593 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.82
Solubility : 1.86 mg/ml ; 0.015 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 2239-83-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2239-83-0 ]

* 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.

  • Upstream synthesis route of [ 2239-83-0 ]
  • Downstream synthetic route of [ 2239-83-0 ]

[ 2239-83-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 90905-33-2 ]
  • [ 2239-83-0 ]
YieldReaction ConditionsOperation in experiment
51% With sodium tetrahydroborate In methanol at 0 - 15℃; for 3 h; To a mixture of 2-methylpyrimidine-5-carbaldehyde (8 g, 66 mmol, compound 44b) in MeOH (100 mL) was added NaBH4 (7.5 g, 197 mmol) at 0 °C, and the resulting reaction mixture was stirred at 15°C for 3 hrs. Then the reaction mixture was quenched by saturated NH4C1 solution (30 mL), extracted by ethyl acetate (20 mL) three times. The separated organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford (2-methylpyrimidin-5-yl)methanol (4.1 g, 51percent, compound 44c) as a white solid.
39% at 0 - 20℃; for 1 h; A solution of 2-methyl-pyrimidine-5-carbaldehyde (5 g, 41 mmol) in MeOH (100 mL) was added NaBH4 (2.3 g, 61.5 mmol) at 0° C. in portions and the resulting mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to give the remains, which was suspended in H2O (20 mL) and extracted with EtOAc (5×50 ml). The organic layer was dried over Na2SO4 and concentrated to afford the title compound (2 g, yield: 39percent). 1H NMR (CDCl3 400 MHz): δ8.64 (s, 2H), 4.72 (s, 2H), 2.73 (s, 3H).
Reference: [1] Patent: WO2016/180695, 2016, A1, . Location in patent: Page/Page column 153
[2] Patent: US2014/107340, 2014, A1, . Location in patent: Paragraph 0121
[3] Patent: US2008/275037, 2008, A1, . Location in patent: Page/Page column 29
[4] Patent: WO2010/33168, 2010, A2, . Location in patent: Page/Page column 80-81
  • 2
  • [ 5194-32-1 ]
  • [ 2239-83-0 ]
YieldReaction ConditionsOperation in experiment
62.6% at 20℃; for 3 h; Step 1 (2-methylpyrimidin-5-yl)methanol To a solution of 2-methylpyrimidine-5-carboxylic acid (150 mg, 1.23 mmOl) in ethanol (5 mL) was added sodium borohydride(93 mg, 2.46 mmol). The mixture was stirred at room temperature for 3 h. It was quenched with aqueous HC1 (2 N, 2 mL), extracted with DCM, dried over sodium sulfate, filtered and concentrated give the yellow oil product (2-methylpyrimidin-5-yl)methanol (95 mg, 62.6percent). LCMS MH+ 125.
62.6% With sodium tetrahydroborate In ethanol at 20℃; for 3 h; To a solution of 2-methylpyrimidine-5-carboxylic acid (150 mg, 1.23 mml) in ethanol (5 mL) was added sodium borohydride (93 mg, 2.46 mmol).
The mixture was stirred at room temperature for 3 h.
It was quenched with aqueous HCl (2 N, 2 mL), extracted with DCM, dried over sodium sulfate, filtered and concentrated give the yellow oil product (2-methylpyrimidin-5-yl)methanol (95 mg, 62.6percent). LCMS MH+ 125.
Reference: [1] Patent: WO2014/143799, 2014, A2, . Location in patent: Page/Page column 387
[2] Patent: US2014/275528, 2014, A1, . Location in patent: Paragraph 0309; 0310
  • 3
  • [ 126504-91-4 ]
  • [ 126504-92-5 ]
  • [ 2239-83-0 ]
Reference: [1] Chemische Berichte, 1990, vol. 123, # 9, p. 1885 - 1889
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