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[ CAS No. 4472-44-0 ] {[proInfo.proName]}

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Chemical Structure| 4472-44-0
Chemical Structure| 4472-44-0
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Product Details of [ 4472-44-0 ]

CAS No. :4472-44-0 MDL No. :MFCD00023199
Formula : C6H7ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :RZVPFDOTMFYQHR-UHFFFAOYSA-N
M.W :142.59 Pubchem ID :20550
Synonyms :

Calculated chemistry of [ 4472-44-0 ]

Physicochemical Properties

Num. heavy atoms : 9
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 : 36.97
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) : 2.04
Log Po/w (XLOGP3) : 1.98
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 1.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.489 mg/ml ; 0.00343 mol/l
Class : Soluble
Log S (Ali) : -2.15
Solubility : 1.02 mg/ml ; 0.00712 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.137 mg/ml ; 0.000959 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 4472-44-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4472-44-0 ]

* 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 [ 4472-44-0 ]
  • Downstream synthetic route of [ 4472-44-0 ]

[ 4472-44-0 ] Synthesis Path-Upstream   1~37

  • 1
  • [ 4472-44-0 ]
  • [ 1558-17-4 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
[2] Journal of Organic Chemistry, 1953, vol. 18, p. 588,591
[3] Journal of the Chemical Society, 1952, p. 4691,4694
[4] Journal of the Chemical Society, 1952, p. 4691,4694
  • 2
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 3
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 4
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 5
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 6
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YieldReaction ConditionsOperation in experiment
91% for 10 h; Inert atmosphere; Reflux The mixture of compound 2 (1998 mg, 12.44mmol) and phosphorus oxychloride (20 mL) was refluxed for 10 h. The remaining phosphorusoxychloride was evaporated to get a brown oil in the flask. The mixture was cooled in an icebath, and concentrated aqueous KOH solution was added dropwise cautiously with stirring,until the litmus paper showed pH value that is approximately 8. Diethyl ether (30 mL) wasadded, and the mixture was stirred for 2.5 h. The water layer was extracted with Et2O (3 × 30mL) and EtOAc (3 × 30 mL). The organic layers were combined, washed with brine, driedover Na2SO4, filtered and concentrated under reduced pressure. The resulting yellow liquidwas put in an ice bath under vacuum to afford compound 3 (1606 mg, 91percent yield) as yellowcrystals. 1H NMR (400 MHz, DMSO-d6) δ 7.33 (s, 1H), 2.42 (s, 6H).
77% With trichlorophosphate In neat (no solvent) for 10 h; Inert atmosphere; Reflux A mixture of 4,6-dimethyl-2-hydroxypyrimidine hydrochloride (20.0 g, 0.125 mol) and phosphorous oxychloride (110 ml) was refluxed for 10 h after which time the residual phosphorous oxychloride was removed in vacuum.
The residual oil was poured into 50 g of ice and was neutralized below 10 °C with a concentrated solution of potassium hydroxide.
The resulting mixture with 300 ml diethyl ether was vigorously stirred for 10 h.
The organic extract was evaporated to dryness.
The residual crude product was recrystallized from a minimal amount of petroleum ether (b.pt. 40-70 °C) giving 13.8 g (77percent) of as colorless 4,6-dimethyl-2-chloropyrimidine plates (m.pt. 37-38 °C).
1H NMR (CDCl3/CCl4) δ 6.89(1H, s), 2.37 (6H, s).
Reference: [1] PLoS ONE, 2018, vol. 13, # 1,
[2] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6550 - 6552
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 4, p. 986 - 991
[4] Journal of Organometallic Chemistry, 2013, vol. 732, p. 137 - 141
  • 7
  • [ 108-79-2 ]
  • [ 4472-44-0 ]
Reference: [1] Patent: WO2006/68213, 2006, A1, . Location in patent: Page/Page column 42
[2] Patent: US6455528, 2002, B1,
[3] Patent: EP1840121, 2007, A1,
[4] Patent: EP2033637, 2009, A1, . Location in patent: Page/Page column 27
[5] Patent: EP2042171, 2009, A1, . Location in patent: Page/Page column 26-27
[6] European Journal of Inorganic Chemistry, 2018, vol. 2018, # 23, p. 2695 - 2701
[7] Patent: EP2039687, 2009, A1, . Location in patent: Page/Page column 27
  • 8
  • [ 767-15-7 ]
  • [ 4472-44-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 343 - 348
[2] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 9, p. 5515 - 5522
[3] Chinese Journal of Chemistry, 2015, vol. 33, # 10, p. 1124 - 1134
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 1, p. 48 - 54
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 1, p. 34 - 41
[6] Letters in Drug Design and Discovery, 2016, vol. 13, # 4, p. 343 - 351
[7] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 167 - 178
[8] Journal of Fluorine Chemistry, 2016, vol. 184, p. 36 - 44
  • 9
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Reference: [1] Patent: US6107301, 2000, A,
  • 10
  • [ 34289-60-6 ]
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YieldReaction ConditionsOperation in experiment
56% for 18 h; Heating / reflux Reference Example 129: 2-Chloro-4,6-dimethyl-pyrimidme. A suspension of 4,6-dimethyl-lH-pyrimidin-2-one hydrochloride (3.0 g, 18.75 mmol) in dry POCl3 (25 mL, 272 mmol) was refluxed for 18 hours. The reaction mixture was evaporated to dryness and the residue dissolved in dichloromethane. The solution was washed with sodium bicarbonate solution until the pH of the aqueous washings were neutral, then with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 2-chloro-4,6-dimethyl-ρyrimidine (1.5 g, 56 percent) as a solid.
Reference: [1] Patent: WO2008/62182, 2008, A1, . Location in patent: Page/Page column 144-145
  • 11
  • [ 149605-42-5 ]
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  • [ 771447-77-9 ]
Reference: [1] Patent: US5266570, 1993, A,
  • 12
  • [ 100-46-9 ]
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  • [ 4472-44-0 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 3, p. 1080 - 1084
  • 13
  • [ 123-54-6 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 343 - 348
[2] PLoS ONE, 2018, vol. 13, # 1,
[3] European Journal of Inorganic Chemistry, 2018, vol. 2018, # 23, p. 2695 - 2701
[4] Patent: WO2008/62182, 2008, A1,
  • 14
  • [ 1134-81-2 ]
  • [ 288-13-1 ]
  • [ 13036-57-2 ]
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  • [ 14164-34-2 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 15
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 16
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Reference: [1] Patent: US6342503, 2002, B1, . Location in patent: Example 1
  • 17
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Reference: [1] Medicinal Chemistry Research, 2015, vol. 24, # 6, p. 2551 - 2560
  • 18
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  • [ 14164-34-2 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 19
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 20
  • [ 7647-01-0 ]
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Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
  • 21
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3581 - 3585
  • 22
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  • [ 138538-42-8 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
  • 23
  • [ 4472-44-0 ]
  • [ 22126-16-5 ]
YieldReaction ConditionsOperation in experiment
82% With 3-quinuclidinol In dimethyl sulfoxide at 70℃; for 6.5 h; General procedure: A mixture of 2-chloropyrimidines(10 mmol), potassium cyanide (13–15 mmol), water (20 mmol), and DMSO(20 mL) was heated to 60 C. A solution of 3-quinuclidinol (0.1–0.2 mmol) inDMSO(5 mL) was added to the reaction mixture over 0.5 h. The reaction mixturewas stirred at 50–70 C for additional hours as specified in Table 1. Uponcompletion, the mixture was cooled to room temperature and water (50 mL) wasadded. The resulting mixture was extracted with isopropyl acetate (3 40 mL)(product 7a precipitated out after water addition and was collected by filtration).The combined organic layers were washed with water (2 30 mL), dried overMgSO4, filtered, and concentrated under vacuum to give crude 2-cyanopyrimidines, which were purified by column chromatography (SiO2) to afford pureproducts.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 36, p. 5055 - 5057
  • 24
  • [ 4472-44-0 ]
  • [ 4637-24-5 ]
  • [ 14001-61-7 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 2, p. 465 - 474
  • 25
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  • [ 124-41-4 ]
  • [ 14001-61-7 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
  • 26
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  • [ 23906-13-0 ]
YieldReaction ConditionsOperation in experiment
52% With hydrazine hydrate In ethanol at 20℃; for 2 h; Hydrazine monohydrate (1.02 mL, 21.0 mmol) was added to a solution of 2-chloro 4,6-dimethylpyrimidine (2 g, 14.0 mmol) in ethanol (5 mL). The mixture was allowed to stir at room temperature for 2 h. The precipitate that formed was collected by filtration and washed with methanol. The solid was allowed to dry in a stream of air to afford 1 g of 2- hydrazinyl-4,6-dimethylpyrimidine as a white solid (1 g). Yield: 52percent; m/z (ESI+) 139 (MH+).
Reference: [1] Patent: WO2012/154880, 2012, A1, . Location in patent: Page/Page column 60
[2] Journal of the Chemical Society, 1952, p. 4691,4694
[3] Farmaco, Edizione Scientifica, 1956, vol. 11, p. 389,393
[4] Farmaco, Edizione Scientifica, 1983, vol. 38, # 4, p. 255 - 264
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1989, vol. 25, # 12, p. 1369 - 1373[6] Khimiya Geterotsiklicheskikh Soedinenii, 1989, # 12, p. 1644 - 1648
[7] Medicinal Chemistry Research, 2015, vol. 24, # 6, p. 2551 - 2560
[8] European Journal of Inorganic Chemistry, 2018, vol. 2018, # 23, p. 2695 - 2701
  • 27
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  • [ 201230-82-2 ]
  • [ 27427-89-0 ]
Reference: [1] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0586; 0587; 0588
  • 28
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  • [ 16490-02-1 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
  • 29
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Reference: [1] Russian Journal of General Chemistry, 2002, vol. 72, # 3, p. 464 - 471
  • 30
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Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
[2] Journal of the Chemical Society, 1946, p. 362,365
  • 31
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  • [ 57-68-1 ]
Reference: [1] Yakugaku Zasshi, 1949, vol. 69, p. 491[2] Chem.Abstr., 1950, p. 3456
[3] Yakugaku Zasshi, 1951, vol. 71, p. 1420[4] Chem.Abstr., 1952, p. 8095
  • 32
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  • [ 63-74-1 ]
  • [ 57-68-1 ]
Reference: [1] Yakugaku Zasshi, 1950, vol. 70, p. 283,284[2] Chem.Abstr., 1951, p. 2894
  • 33
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  • [ 108-79-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1989, vol. 25, # 12, p. 1369 - 1373[2] Khimiya Geterotsiklicheskikh Soedinenii, 1989, # 12, p. 1644 - 1648
  • 34
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  • [ 64-17-5 ]
  • [ 22325-27-5 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
  • 35
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  • [ 54198-72-0 ]
Reference: [1] Patent: WO2013/142269, 2013, A1,
  • 36
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  • [ 74502-83-3 ]
Reference: [1] Patent: WO2013/142269, 2013, A1,
  • 37
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  • [ 22236-10-8 ]
Reference: [1] Patent: US4783459, 1988, A,
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