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[ CAS No. 1780-31-0 ] {[proInfo.proName]}

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Product Details of [ 1780-31-0 ]

CAS No. :1780-31-0 MDL No. :MFCD00023197
Formula : C5H4Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :DQXNTSXKIUZJJS-UHFFFAOYSA-N
M.W :163.00 Pubchem ID :74508
Synonyms :

Calculated chemistry of [ 1780-31-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.02
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) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.49
Log Po/w (WLOGP) : 2.09
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 2.67
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.199 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (Ali) : -2.68
Solubility : 0.343 mg/ml ; 0.00211 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0892 mg/ml ; 0.000547 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 1780-31-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1780-31-0 ]

* 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 [ 1780-31-0 ]
  • Downstream synthetic route of [ 1780-31-0 ]

[ 1780-31-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1780-31-0 ]
  • [ 2036-41-1 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 829,833,835
  • 2
  • [ 1780-31-0 ]
  • [ 50840-23-8 ]
Reference: [1] Patent: WO2013/132376, 2013, A1,
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4720 - 4744
  • 3
  • [ 1780-31-0 ]
  • [ 22536-61-4 ]
YieldReaction ConditionsOperation in experiment
78% With zinc In water for 3 h; Reflux Step 1 : A suspension of compound 242 (50.0 g, 307 mmol) and freshly activated (acid washed) Zn (59.8 g, 920 mmol) in water (500 mL) was heated at reflux for 3 hours. TLC showed consumption of SM. The reaction mixture was cooled to room temperature, filtered through a pad of celite, and rinsed with CH2CI2 (500 mL). The phases of the filtrate were separated and the organic phase was washed with brine (300 mL), dried over MgS04, filtered and concentrated under vacuum carefully to give compound 243 as a beige powder (30.6 g, 78percent yield, 95percent purity by 1 H NMR).1 H NMR (400 MHz, DMSO-d6) δ 8.63 (d, J = 0.9 Hz, 2H), 2.27 (t, J = 0.8 Hz, 3H).
77% With ammonium hydroxide; zinc In water; benzene for 18 h; Reflux Step 1.
Preparation of 2-chloro-5-methylpyrimidine
To a stirred solution of 2,4-dichloro-5-methylpyrimidine (4.00 g, 24.5 mmol) in a mixture of benzene (16.0 mL) and H2O (40.0 mL) was added zinc powder (4.81 g, 73.6 mmol) and ammonia water (8.80 mL, 24.5 mmol) at room temperature.
After heating at reflux for 18 hours, the reaction mixture was cooled and filtered through a pad of Celite and the reaction mixture was extracted with Et2O, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo.
The residue was purified by column chromatography on SiO2 (Hexanes:EtOAc=1:1) to give the desired product (2.44 g, 77percent) as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ 2.33 (3H, s), 8.47 (2H, s).
75% Reflux A mixture of 2,4-dichloro-5-methylpyrimidine (50 g, 0.31 mol), water (500 mL) and zinc dust (50 g, 0.94 mol) was heated at reflux overnight.
The reaction mixture was filtered and the filtrate was extracted with dichloromethane (3*500 mL).
The organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo.
The residue was recrystallized from petroleum ether to afford compound C60 as a white solid. Yield: 27.9 g, 0.22 mol, 75percent. LCMS m/z 129.3 (M+1).
1H NMR (400 MHz, CDCl3) δ 2.25 (s, 3H), 8.40 (5, 2H).
69%
Stage #1: With acetic acid; zinc In tetrahydrofuran for 3.66667 h;
Stage #2: With sodium hydroxide; water In dichloromethane; ethyl acetate
EXAMPLE 84[4-(6-Bromobenzo[b]thiophen-2-yl)-5-methylpyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine tri-hydrochloride(A). Preparation of 2-chloro-5-methylpyrimidine; Into a 3-necked, 500 mL round bottomed flask is added 2,4-dichloro-5-methylpyrimidine (25.0 g, 153 mmol), THF (125 mL) and zinc powder (30.1 g, 460 mmol). The mixture is heated to reflux and acetic acid (HOAc) (9.21 g, 153 mmol) in THF (20 mL) is dropwise added over 1 hour. After 1.5 hours at reflux, additional HOAc (3.93 g, 65.5 mmol) in THF (12.5 mL) is added over 10 minutes, and the mixture is refluxed for an additional 1 hour. The mixture is filtered over celite, rinsed with THF (150 mL) and the organic layers are concentrated under reduced pressure. The crude mixture is partitioned in EtOAc/dichloromethane/1 N NaOH and filtered. The organic layer is concentrated under reduced pressure to yield a peach colored solid. The crude material is subjected to chromatography on silica (in hexane) to provide the title compound as a white solid (13.5 g, 69percent yield).

Reference: [1] Patent: WO2013/132376, 2013, A1, . Location in patent: Page/Page column 224
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4720 - 4744
[3] Patent: US2012/53180, 2012, A1, . Location in patent: Page/Page column 8
[4] Patent: US2010/190771, 2010, A1, . Location in patent: Page/Page column 33
[5] Patent: US2008/306082, 2008, A1, . Location in patent: Page/Page column 26-27
[6] Patent: WO2004/22553, 2004, A1, . Location in patent: Page/Page column 34
[7] Patent: WO2008/85316, 2008, A1, . Location in patent: Page/Page column 97
[8] Patent: US2005/234046, 2005, A1, . Location in patent: Page/Page column 63
  • 4
  • [ 65-71-4 ]
  • [ 1780-31-0 ]
YieldReaction ConditionsOperation in experiment
48% for 3 h; Reflux 6-Methyluracyl (1 g, 7.93 mmol) was added to phosphoryl chloride (7 eq, 5 ml) and the mixture was heated at reflux for 3 h. The mixture was poured onto ice and the organic layer was extracted with chloroform (3times, 20 ml) and dried over anhydrous MgSO4. The solvents were evaporated to give the dichloride as yellow crystals (0.62 g, 48percent). 1H NMR (400 MHz, CDCI3) 5 8.35 (s, 1 H), 2.39(s, 3H); 13C NMR (100 MHz, CDCI3) 6 162.5, 160.0,158.2, 129.1, 15.8. The 1H NMR spectrum was in accordance with literature:Wang, H., K. Wen, L. Wang, Y. Xiang, X. Xu, Y. Shen and Z. Sun (2012).Molecules, 2012, 17(4), 4533-4544.
Reference: [1] Journal of Fluorine Chemistry, 1996, vol. 77, # 1, p. 93 - 95
[2] Patent: WO2018/151681, 2018, A1, . Location in patent: Paragraph 0099
[3] Synthetic Communications, 1992, vol. 22, # 20, p. 2927 - 2934
[4] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1111 - 1114
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 18, p. 2961 - 2966
[6] Patent: US5525724, 1996, A,
[7] Patent: EP714896, 1996, A1,
[8] Patent: US2005/234046, 2005, A1, . Location in patent: Page/Page column 63
  • 5
  • [ 65-71-4 ]
  • [ 1780-31-0 ]
Reference: [1] Molecules, 2012, vol. 17, # 4, p. 4533 - 4544
[2] Organic and Biomolecular Chemistry, 2003, vol. 1, # 19, p. 3353 - 3361
[3] Chemische Berichte, 1905, vol. 38, p. 3397
[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1900, vol. 29, p. 304
  • 6
  • [ 1780-31-0 ]
  • [ 20090-58-8 ]
  • [ 14394-70-8 ]
Reference: [1] Patent: WO2004/74278, 2004, A1, . Location in patent: Page 31-33
  • 7
  • [ 1780-31-0 ]
  • [ 54-20-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1996, vol. 77, # 1, p. 93 - 95
  • 8
  • [ 1780-31-0 ]
  • [ 20090-58-8 ]
  • [ 14394-70-8 ]
Reference: [1] Patent: WO2004/74278, 2004, A1, . Location in patent: Page 31-33
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