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[ CAS No. 57054-92-9 ] {[proInfo.proName]}

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Chemical Structure| 57054-92-9
Chemical Structure| 57054-92-9
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Product Details of [ 57054-92-9 ]

CAS No. :57054-92-9 MDL No. :MFCD03001373
Formula : C5H4BrClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :ZPPORMCRNCNFGX-UHFFFAOYSA-N
M.W : 223.46 Pubchem ID :3663143
Synonyms :

Calculated chemistry of [ 57054-92-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.23
TPSA : 35.01 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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 1.9
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 2.25
Consensus Log Po/w : 1.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.243 mg/ml ; 0.00109 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.663 mg/ml ; 0.00297 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.124 mg/ml ; 0.000555 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 57054-92-9 ]

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 [ 57054-92-9 ]

* 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 [ 57054-92-9 ]
  • Downstream synthetic route of [ 57054-92-9 ]

[ 57054-92-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 36082-50-5 ]
  • [ 124-41-4 ]
  • [ 57054-92-9 ]
YieldReaction ConditionsOperation in experiment
93% at 20℃; for 4 h; A 30percent solution of sodium methoxide in methanol (8.0 mL, 42.0 mmol) was added dropwise to a cooled (ice-bath) solution of 5-bromo-2,4-dichloropyrimidine (9.85 g, 43.2 mmol) in methanol (100 mL). The mixture was warmed to room temperature and stirred for 4 hours. The solvent was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was washed with water, brine, dried (MgS04) and evaporated to give the title compound (9.40 g, 93percent) as a solid.LRMS (m/z): 222/224 (M+1)+.H-NMR δ (CDCI3): 4.1 1 (s, 3H), 8.44 (s, 1 H).
93% at 20℃; for 4 h; Cooling with ice   sodium methoxide in   methanol (8.0 mL, 42.0 mmol) was added dropwise to a cooled (ice-bath) solution of   5-bromo-2,4-dichloropyrimidine (9.85 g, 43.2 mmol) in methanol (100 mL). The mixture was warmed to room temperature and stirred for 4 hours. The solvent was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was washed with water, brine, dried (MgSO4) and evaporated to give the title compound (9.40 g, 93percent) as a   solid.LRMS (m/z): 222/224 (M+1)+.1H-NMR δ (CDCl3): 4.11 (s, 3H), 8.44 (s, 1 H).
90% at 20℃; 5-bromo-2,4-dichloropyrimidine (500mg, 2.194mmol) was dissolved in anhydrous methanol (5mL) in, under nitrogen, was added dropwise sodium methoxide (sodium 56mg, 2.42mmol) in methanol (1.85 mL) And stirred overnight at room temperature. Saturated ammonium chloride solution was added to quench the reaction, recovery of the solvent under reduced pressure, added to the washed CH2Cl2 (30mL), washed with water (30 mL) under reduced pressure to recover the solvent. Purification by silica gel column chromatography eluting with PE: EtOAc (4: 1) gave a white solid. Yield: 90percent;
88% at 20℃; for 2 h; To a stirred solution of 5-bromo-2,4-dichloropyrimidine (500 mg, 2.19 mmol) in MeOH (5 mL) was added a 30percent solution of sodium methoxide (0.40 mL, 2.26 mmol). The reaction mixture was stirred at RT for 2 h then concentrated. The residue was dissolved in water (5 mL) and extracted with EA (3 x 5 mL). The combined organic layer was washed with brine, dried over MgS04 and concentrated to afford 432 mg (88percent) of 5-bromo-2-chloro-4-methoxypyrimidine as white solid. LCMS- ESI (m/z) calculated for C5H4BrClN20: 223.4; found 224.2 [M+H]+, tR = 7.66 min. (Method 2).
88% at 20℃; for 2 h; [006451 To a stined solution of 5-bromo-2,4-dichloropyrimidine (500 mg, 2.19 mmol) in MeOH (5 mL) was added a 30percent solution of sodium methoxide (0.40 mL, 2.26 rnrnol). The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was dissolved in water (5 mL) and extracted with EA (3 x 5 mL). The combined organic layer was washed with brine, dried over MgSO4 and concentrated to afford 432 mg (88percent) of 5-brorno-2-chloro-4-rnethoxypyrimidine as white solid. LCMS-ESI (rnIz) calculated for C5H4BrCIN7O: 223.4; found 224.2 [M+H], 1R = 7.66 mm. (Method 2).
86% at 0 - 23℃; Intermediate 26: 5-Bromo-2-chloro-4-(methyloxy)pyrimidineTo a solution of 5-bromo-2,4-dichloropyrimidine (17.82 g, 78.2 mmol) in methanol (100 mL) stirred at 0 °C was added solid sodium methoxide (4.22 g, 78 mmol) portionwise during 5 minutes. The reaction mixture was stirred at 23 °C overnight. To the organic phase was added water (25 mL) and the methanol was removed. Then it was extracted with dichloromethane. The organic phase was dried over sodium sulphate and evaporated in vacuo to give the title compound as a white solid (17.2 g, 67.6 mmol, 86 percent yield). LC/MS [M+H]+ = 223/225.
76% at -78 - 0℃; for 1 h; To a cooled (-78 °C) solution of 5-bromo-2,4-dichloropyrimidine (1.7 g, 7.3 mmol) in THF (30mL) was added dropwise a 25 wtpercent solution of methylamine in ethanol (1.7 mL). The reaction was allowed to warm to 0 °C and stirred for 1 h. The reaction was then concentrated and re-dissolved in EtOAc. The solution was washed with brine, dried over Na2S04, filtered and concentrated to give 5-bromo-2-chloro-4-methoxypyrimidine (1.25 g, 76percent). 1H- MR (CDC13): 6 8.43 (s, 1H), 4.10 (s, 3H).

Reference: [1] Patent: WO2011/76419, 2011, A1, . Location in patent: Page/Page column 119
[2] Patent: EP2338888, 2011, A1, . Location in patent: Paragraph 0173; 0174
[3] Tetrahedron Letters, 2006, vol. 47, # 26, p. 4415 - 4418
[4] Patent: CN106588884, 2017, A, . Location in patent: Paragraph 0299; 0303; 0304; 0305
[5] Patent: WO2013/90454, 2013, A2, . Location in patent: Paragraph 00386
[6] Patent: WO2016/94729, 2016, A1, . Location in patent: Paragraph 00645
[7] Patent: WO2012/55942, 2012, A1, . Location in patent: Page/Page column 50
[8] Patent: WO2012/62783, 2012, A1, . Location in patent: Page/Page column 62
[9] Patent: US2006/199817, 2006, A1, . Location in patent: Page/Page column 49
[10] Patent: WO2010/38081, 2010, A2, . Location in patent: Page/Page column 86-87
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