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[ CAS No. 1780-32-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1780-32-1
Chemical Structure| 1780-32-1
Chemical Structure| 1780-32-1
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Product Details of [ 1780-32-1 ]

CAS No. :1780-32-1 MDL No. :MFCD09910263
Formula : C6H6Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :BFXIDUSEHNCLTP-UHFFFAOYSA-N
M.W : 177.03 Pubchem ID :241553
Synonyms :

Calculated chemistry of [ 1780-32-1 ]

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 : 41.98
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) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 2.89
Log Po/w (WLOGP) : 2.4
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 2.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.111 mg/ml ; 0.000628 mol/l
Class : Soluble
Log S (Ali) : -3.09
Solubility : 0.143 mg/ml ; 0.00081 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.66
Solubility : 0.0391 mg/ml ; 0.000221 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 1780-32-1 ]

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

Application In Synthesis of [ 1780-32-1 ]

* 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 [ 1780-32-1 ]
  • Downstream synthetic route of [ 1780-32-1 ]

[ 1780-32-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 1780-32-1 ]
  • [ 1193-74-4 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 2813
  • 2
  • [ 1780-32-1 ]
  • [ 54568-12-6 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 2813
  • 3
  • [ 26305-13-5 ]
  • [ 1780-32-1 ]
YieldReaction ConditionsOperation in experiment
98% for 4 h; Reflux 5,6-Dimethyl-1H-pyrimidin-2,4-dione (2.5 g, 17.8 mmol) was dissolved in 12 mL of phophorus oxychloride, andthe mixture was stirred for 4 hours under reflux. The reaction solution was cooled to at room temperature and added tocold water. The formed precipitate was dried to obtain the title compound (3.08 g, 98 percent).1H-NMR (DMSO-d6) δ 2.51 (3H, s), 2.30 (3H, s)
87% With trichlorophosphate In N,N-dimethyl-formamide at 110℃; for 23 h; 2,4-Dichloro-5,6-dimethylpyrimidine (RJ1-008) (WO2013/123401): A mixture of RJ1-006 (4.00 g, 28.5 mmol), phosphorus(V) oxychloride (60 mL, 0.642 mol), and dimethylformamide (0.08 mL, 1.03 mmol) was heated to reflux at 110 °C for 23 hours. The reaction mixture was then cooled to ambient temperature and evaporated. Toluene (80 mL) was added to the residue and the resulting mixture was concentrated. Cold water with ice (160 mL) was added to the residue, and the mixture was extracted with chloroform (3 x 60 mL). The combined organic layers were washed with brine (2 x 150 mL), dried over sodium sulfate, filtered, and concentrated to provide RJ1-008 as a pale yellow solid (4.37 g, 87percent). m.p. = 68-70 °C. XH NMR (400 MHz, CDCb) δ 2.55 (s, 3H), 2.34 (s, 3H). LRMS (ESI+) m/z 177.1
87% at 110℃; for 23 h; A mixture of RJ1-006 (4.00 g, 28.5 mmol), phosphorus(V) oxychloride (60 mL, 0.642 mol), and dimethylformamide (0.08 mL, 1.03 mmol) was heated to reflux at 110 °C for 23 hours. The reaction mixture was then cooled to ambient temperature and evaporated. Toluene (80 mL) was added to the residue and the resulting mixture was concentrated. Cold water with ice (160 mL) was added to the residue, and the mixture was extracted with chloroform (3 x 60 mL). The combined organic layers were washed with brine (2 x 150 mL), dried over sodium sulfate, filtered, and concentrated to provide RJ1- 008 as a pale yellow solid (4.37 g, 87percent). m.p. = 68-70 °C. NMR (400 MHz, CDCb) δ 2.55 (s, 3H), 2.34 (s, 3H). LRMS (ESI+) m/z 177.1 (MC135C135+H)+, 179.0 (MC135C137+H)+, 181.0 (MC137C137+H)+.
73% Reflux; Inert atmosphere To a stirred solution of 5,6-dimethylpyrimidine-2,4(l f,3H)-dione (10.3 g, 0.07 mol, Step B) in phosphorus(V) oxychloride (150 mL) was added dimethylformamide (0.2 ml). The resulting mixture was refluxed overnight under argon and cooled down to ambient temperature. The resulting mixture was evaporated. Toluene (200 mL) was added to the residue. The resulting mixture was concentrated. Cold water with ice (400 mL) was added to the residue, and the mixture was extracted with chloroform (3 x 150 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane mixture (1 :2-l : 1) to yield 9.5 g (73percent) of the titled compound. H NMR (400 MHz, CDC13) δ ppm 2.35 (s, 3H) 2.55 (s, 3H).

Reference: [1] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0503
[2] Patent: WO2016/22460, 2016, A1, . Location in patent: Page/Page column 140-141
[3] Patent: WO2017/66428, 2017, A1, . Location in patent: Page/Page column 253
[4] Patent: WO2013/123401, 2013, A1, . Location in patent: Page/Page column 40
[5] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 11, p. 1707 - 1721
[6] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 510 - 524
[7] Molecules, 2011, vol. 16, # 6, p. 5113 - 5129
[8] Chemistry and Biodiversity, 2011, vol. 8, # 8, p. 1455 - 1469
  • 4
  • [ 26305-13-5 ]
  • [ 1780-32-1 ]
YieldReaction ConditionsOperation in experiment
92.6% for 6 h; Inert atmosphere A mixture of 5,6-dimethylpyrimidine- 2,4-diol (10 g, 71.36 mmol) in POCl3 (100 ml) was stirred at 100 °C for 6 h under N2. TLC showed the reaction was complete. The reaction was concentrated in vacuo. The crude product was diluted with DCM (100 mL), aq.NaHCO3 (200 mL) was added to adjust pH=8, separated and extracted with DCM (100 mL x 3). The combined organic layers were dried over Na2SO4, and concentrated in vacuo and purified by column (hexane and ethyl acetate) to afford 2,4-dichloro-5,6-dimethyl-pyrimidine (13 g, 92.6percent) as a white solid.
64.7% With trichlorophosphate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; <i>N</i>,<i>N</i>-dimethyl-aniline Step 1
5,6-Dimethyl-2,4-dichloropyrimidine
A mixture solution of 5,6-dimethyl-2,4-dihydroxypyrimidine(72 g, 0.51 mol), phosphorous oxychloride(250 ml) and N,N-dimethylaniline(41 ml) was heated to reflux for 3 hours and cooled to room temperature.
The reaction mixture was added to ice water and the resulting solid was filtered and recrystallized from dichloromethane to give 58.5 g of the titled compound. (Yield: 64.7percent)
60% With trichlorophosphate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; <i>N</i>,<i>N</i>-dimethyl-aniline Step 1
5,6-Dimethyl-2,4-dichloropyrimidine
A mixture solution of 5,6-dimethyl-2,4-dihydroxy pyrimidine(72 g, 0.51 mol), phosphorus oxychloride(250 ml) and N,N-dimethylaniline(41 ml) was heated to reflux for 3 hours.
After cooling to room temperature, the reaction mixture was added slowly to ice water.
The resulting solid was filtered and recrystallized from dichloromethane to give 54.3 g of the titled compound. (Yield: 60percent)
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2011, vol. 30, # 4, p. 293 - 315
[2] Patent: WO2016/200840, 2016, A1, . Location in patent: Page/Page column 414
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5735 - 5738
[4] Patent: US5750531, 1998, A,
[5] Patent: US5750531, 1998, A,
  • 5
  • [ 121-69-7 ]
  • [ 26305-13-5 ]
  • [ 1780-32-1 ]
YieldReaction ConditionsOperation in experiment
92% at 125℃; for 3 h; Heating / reflux Step A:
Synthesis of 2,4-dichloro-5,6-dimethyl-pyrimidine.
To a suspension of 2,4-dihydroxy-5,6-dimethylpyrimidine (6.2 g, 0.044 mol) in POCl3 (25 mL) was slowly added N,N-dimethylaniline (6.18 mL, 0.049 mol).
The mixture was then refluxed at 125 °C for 3 hours.
After this time, the starting material completely dissolved indicating that the reaction was completed.
The reaction mixture was cooled and then poured slowly onto ice to quench the POCl3 (caution[exothermic]).
A precipitate formed, which was filtered and washed with ice-cold water.
The precipitate was dried under high vacuum overnight to yield 2,4-dichloro-5,6-dimethyl-pyrimidine (7.2 g, 0.041 mol, 92 percent) as a yellow solid.
1H NMR (400 MHz, CDCl3) δ 2.56 (s, 3H), 2.36 (s, 3H).
Reference: [1] Patent: EP1464335, 2004, A2, . Location in patent: Page/Page column 318
  • 6
  • [ 609-14-3 ]
  • [ 1780-32-1 ]
Reference: [1] Patent: WO2013/123401, 2013, A1,
  • 7
  • [ 28456-54-4 ]
  • [ 1780-32-1 ]
Reference: [1] Patent: WO2013/123401, 2013, A1,
  • 8
  • [ 26305-13-5 ]
  • [ 10025-87-3 ]
  • [ 1780-32-1 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 2813
  • 9
  • [ 67-56-1 ]
  • [ 1780-32-1 ]
  • [ 120129-83-1 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2011, vol. 30, # 4, p. 293 - 315
[2] Molecules, 2011, vol. 16, # 6, p. 5113 - 5129
  • 10
  • [ 1780-32-1 ]
  • [ 124-41-4 ]
  • [ 120129-83-1 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 11, p. 1707 - 1721
[2] Chemische Berichte, 1901, vol. 34, p. 2813
[3] Chemische Berichte, 1901, vol. 34, p. 2813
[4] Chemistry and Biodiversity, 2011, vol. 8, # 8, p. 1455 - 1469
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