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[ CAS No. 69696-35-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 69696-35-1
Chemical Structure| 69696-35-1
Chemical Structure| 69696-35-1
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Product Details of [ 69696-35-1 ]

CAS No. :69696-35-1 MDL No. :MFCD13705450
Formula : C6H6BrClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :BZQXOFCIHJDLCR-UHFFFAOYSA-N
M.W : 221.48 Pubchem ID :12490576
Synonyms :

Calculated chemistry of [ 69696-35-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.67
TPSA : 25.78 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) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 2.66
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 1.65
Log Po/w (SILICOS-IT) : 3.09
Consensus Log Po/w : 2.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.103 mg/ml ; 0.000465 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.311 mg/ml ; 0.0014 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.9
Solubility : 0.0277 mg/ml ; 0.000125 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 69696-35-1 ]

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 [ 69696-35-1 ]

* 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 [ 69696-35-1 ]
  • Downstream synthetic route of [ 69696-35-1 ]

[ 69696-35-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 858269-28-0 ]
  • [ 69696-35-1 ]
YieldReaction ConditionsOperation in experiment
63% at 110℃; for 3 h; b) 5-bromo-4-chloro-2,6-dimethylpyrimidine. A mixture of 5-bromo-2,6- dimethylpyrimidin-4-ol (3.95 g, 19.45 mmol) and phosphorus oxychloride (6 mL, 64.4 mmol) was heated at 1 10 °C for 3h. The solution was concentrated, and water was then added slowly and cautiously to afford a precipitate. The solid was filtered and washed with water, and dried to give the title compound (2.73 g, 63percent). LCMS (ES+) m/e 221 [M+H]+.
48% at 110℃; for 18 h; 5-Bromo-4-chloro-2,6-dimethylpyrimidine (B1.2) (0348) A mixture of B1.1 (134 g, 0.66 mol) in 500 mL of POCl3 was stirred at 110° C. for 18 h. Excess POCl3 was removed under vacuum, the residue was poured into 1000 g crushed ice. Then solid NaHCO3 was added carefully to adjust pH to 8-9. The aqueous was extracted with ethyl acetate (1.5 L×3), and the combined organic layers were washed with brine (1.0 L×2), dried over Na2SO4, concentrated to give the title compound (71 g, 48percent) as a white solid. LC-MS: [M+H]+=223.0.
48% at 110℃; for 18 h; A mixture of B16.2 (134 g, 0.66 mol) in 500 mL of POCl3 was stirred at 110 C for 18 h. Excess POCl3 was removed under vacuum, the residue was poured into 1000 g crushed ice. Then solid NaHCO3 was added carefully to adjust pH to 8-9. The aqueous was extracted with ethyl acetate (1.5 L × 3), and the combined organic layers were washed with brine (1.0 L × 2), dried over Na2SO4, concentrated to give the title compound (71 g, 48percent) as a white solid. LC-MS: [MH]+ = 223.
48% at 110℃; for 18 h; A mixture of BI .1(134 g,0.66 mol) in 500 mL of POd3 was stirred at 110 °C for 18 h. Excess POd3 wasremoved under vacuum, the residue was poured into 1000 g crushed ice. Then solid NaHCO3 was added carefully to adjust pH to 8-9. The aqueous was extracted with ethyl acetate (1 .5 L x 3), and the combined organic layers were washed with brine (1 .0 L x 2), dried over Na2SO4, concentrated to give the title compound (71 g, 48percent) as a white solid. LC-MS: [M+H] = 223.0.

Reference: [1] Patent: WO2013/96151, 2013, A1, . Location in patent: Page/Page column 131
[2] Patent: US2016/176882, 2016, A1, . Location in patent: Paragraph 0346; 0348
[3] Patent: WO2017/221092, 2017, A1, . Location in patent: Paragraph 00202
[4] Patent: WO2017/221100, 2017, A1, . Location in patent: Paragraph 00160
  • 2
  • [ 6622-92-0 ]
  • [ 69696-35-1 ]
Reference: [1] Patent: WO2013/96151, 2013, A1,
[2] Patent: US2016/176882, 2016, A1,
[3] Patent: WO2017/221092, 2017, A1,
[4] Patent: WO2017/221100, 2017, A1,
  • 3
  • [ 858269-28-0 ]
  • [ 69696-35-1 ]
Reference: [1] Yakugaku Zasshi, 1937, vol. 57, p. 579,581; dtsch. Ref. S. 109, 111[2] Chem.Abstr., 1937, p. 6238
  • 4
  • [ 6622-92-0 ]
  • [ 69696-35-1 ]
Reference: [1] Yakugaku Zasshi, 1937, vol. 57, p. 579,581; dtsch. Ref. S. 109, 111[2] Chem.Abstr., 1937, p. 6238
  • 5
  • [ 69696-35-1 ]
  • [ 69696-37-3 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With toluene-4-sulfonic acid hydrazide In chloroform at 90℃; for 16 h;
Stage #2: at 90℃; for 1.5 h;
c) 5-bromo-2,4-dimethylpyrimidine. A mixture of 5-bromo-4-chloro-2,6- dimethylpyrimidine (2.73 g, 12.33 mmol), 4-methylbenzenesulfonohydrazide (4.19 mL, 37.0 mmol) and chloroform (40 mL) was heated at 90 °C for 16 hours. The solution was cooled and the solid filtered and washed with chloroform. LCMS revealed this solid (4.75g) was the desired intermediate. A mixture of this solid and 0.94M aqueous sodium carbonate (40 mL, 37.7 mmol) was heated at 90 °C for 1 .5 hours. The cooled solution was extracted with ethyl acetate 3 times, and the combined organics were washed with brine, dried (Na2S04) and concentrated to afford the title compound (1 .17 g, 51 percent) as a tan oil, which crystallized upon standing. LCMS (ES+) m/e 187 [M+H]+.
Reference: [1] Synthesis, 1984, # 3, p. 252 - 254
[2] Patent: WO2013/96151, 2013, A1, . Location in patent: Page/Page column 131
[3] Patent: US2016/176882, 2016, A1,
[4] Patent: WO2017/221092, 2017, A1,
[5] Patent: WO2017/221100, 2017, A1,
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