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[ CAS No. 956034-07-4 ] {[proInfo.proName]}

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Chemical Structure| 956034-07-4
Chemical Structure| 956034-07-4
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Product Details of [ 956034-07-4 ]

CAS No. :956034-07-4 MDL No. :MFCD11520866
Formula : C6H2Cl2N2O Boiling Point : -
Linear Structure Formula :- InChI Key :OTFDNOQBJWBJJM-UHFFFAOYSA-N
M.W : 189.00 Pubchem ID :45789968
Synonyms :

Calculated chemistry of [ 956034-07-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.82
TPSA : 38.92 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 2.62
Log Po/w (WLOGP) : 2.53
Log Po/w (MLOGP) : 0.97
Log Po/w (SILICOS-IT) : 2.72
Consensus Log Po/w : 2.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.27
Solubility : 0.102 mg/ml ; 0.00054 mol/l
Class : Soluble
Log S (Ali) : -3.09
Solubility : 0.155 mg/ml ; 0.000818 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.0317 mg/ml ; 0.000167 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 956034-07-4 ]

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 [ 956034-07-4 ]

* 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 [ 956034-07-4 ]
  • Downstream synthetic route of [ 956034-07-4 ]

[ 956034-07-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 956034-06-3 ]
  • [ 956034-07-4 ]
YieldReaction ConditionsOperation in experiment
54% at 130℃; for 3 h; To furo[3,2-d]pyrimidine-2,4-diol (7J) (1.52 g, 10 mmol) was added dimethyl aniline (1 mL, 8 mmol), phosphorous oxychloride (0.9 mL, 9.65 mmol) and heated at 130 °C for 3h. The reaction mixture was cooled to room temperature and quenched carefully with ice. The solid obtained was collected by filtration washed with water and dried in vacuum to furnish 2,4- dichlorofuro[3,2-d]pyrimidine (7K) (1.02 g, 54percent) as a light brown solid; mp 107.3 °C; NMR (300 MHz, CDC13) δ 8.08 (d, J= 2.2, 1H), 7.02 (d, J = 2.2, 1H).
48% at -40℃; for 48 h; Heating / reflux Furo[3,2-d]pyrimidine-2,4-diol (39 mg, 1.0 eq) was dissolved in POCl3 (1.8 ml).
Mixture was cooled to -40° C. and N,N-diisopropylethylamine (0.45 ml) wad slowly added.
Reaction mixture was then heated to reflux for 48 h, then cooled to room temperature Reaction mixture was poured into ice/water.
Mixture was extracted with ethyl acetate.
The combined organic layers were washed with saturated aq. NaHCO3, dried (Na2SO4) and concentrated to yield 2,4-dichlorofuro[3,2-d]pyrimidine (23 mg, 48percent) which was used in the next reaction without further purification.
48% at -40℃; for 48 h; Heating / reflux Furo[3,2-d]pyrimidine-2,4-diol 36 (39 mg, 1.0 eq) was dissolved in POCl3(1.8 ml). Mixture was cooled to -40 °C and A^V-dusopropylethylamine (0.45 ml) wad slowly added. Reaction mixture was then heated to reflux for 48 h, then cooled to room temperature Reaction mixture was poured into ice/water. Mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated aq. NaHCO3, dried (Na2SO4) and concentrated to yield 2,4-dichlorofuro[3,2-d]pyrimidine 37 (23 mg, 48percent) which was used in the next reaction without further purification.
48%
Stage #1: at -40℃; for 48 h; Heating / reflux
Stage #2: at 20℃;
Furo[3,2-d]pyrimidine-2,4-diol 36 (39 mg, 1.0 eq) was dissolved in POCl3(1.8 ml). Mixture was cooled to -40 0C and iVJV-diisopropylethylamine (0.45 ml) wad slowly added. Reaction mixture was then heated to reflux for 48 h, then cooled to room temperature Reaction mixture was poured into ice/water. Mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated aq. NaHCO3, dried (Na2SO4) and concentrated to yield 2,4-dichlorofuro[3,2-d]pyrimidine 37 (23 mg, 48percent) which was used in the next reaction without further purification.
41% at -40℃; for 24 h; Reflux At −40° C., to a solution of compound 30-d (0.86 g, 5.6 mmoL) in phosphorus oxychloride (8 mL) was added N,N-diisopropylethylamine (2 mL), after stirred for 10 minutes, the mixture was refluxed for 24 hours. After cooled to room temperature, the mixture was poured into ice water to quench the reaction, and then extracted with ethyl acetate (50 mL×3). The organic layers were combined, washed with water (20 mL×3) and saturated brine (20 mL) in sequence, then dried over anhydrous sodium sulfate, filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate-100:1) to give white solid 30-c (430 mg, yield: 41percent). LC-MS (ESI): m/z=189 [M+H]+.

Reference: [1] Patent: WO2011/79230, 2011, A2, . Location in patent: Page/Page column 57
[2] Patent: US2008/76758, 2008, A1, . Location in patent: Page/Page column 78
[3] Patent: WO2008/70740, 2008, A1, . Location in patent: Page/Page column 138
[4] Patent: WO2008/73785, 2008, A2, . Location in patent: Page/Page column 165
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[6] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0240; 0246
  • 2
  • [ 956034-06-3 ]
  • [ 956034-07-4 ]
YieldReaction ConditionsOperation in experiment
87% at 130℃; for 2 h; To a mixture of lH-furo[3,2-d]pyrimidine-2,4-dione (3.0 g, 0.020 mol) in NJf- dimethylaniline (2.0 mL, 0.016 mol) was added phosphorous oxychloride (18.0 mL, 0.193 mol) and the resulting mixture heated at 130 °C for 2 h. The resulting black solution was cooled to RT, then carefully quenched with crushed ice and H2O, then extracted with EtOAc.The organic layer was isolated, dried (MgSO4) and concentrated in vacuo to give the title compound as a tan solid (3.26 g, 87 percent). 1H NMR (400 MHz, CDCl3): δ 7.02 (d, J = 2.2 Hz, 1 H) and 8.08 (d, J = 2.2 Hz, 1 H).
Reference: [1] Patent: WO2008/152394, 2008, A1, . Location in patent: Page/Page column 25; 35
[2] MedChemComm, 2014, vol. 5, # 12, p. 1821 - 1828
  • 3
  • [ 956034-03-0 ]
  • [ 956034-07-4 ]
Reference: [1] Patent: WO2011/79230, 2011, A2,
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[3] Patent: US2015/336982, 2015, A1,
[4] Patent: WO2008/152394, 2008, A1,
  • 4
  • [ 956034-04-1 ]
  • [ 956034-07-4 ]
Reference: [1] Patent: WO2011/79230, 2011, A2,
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[3] Patent: US2015/336982, 2015, A1,
[4] Patent: WO2008/152394, 2008, A1,
  • 5
  • [ 1093066-63-7 ]
  • [ 956034-07-4 ]
Reference: [1] Patent: WO2011/79230, 2011, A2,
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[3] Patent: US2015/336982, 2015, A1,
[4] Patent: WO2008/152394, 2008, A1,
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