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[ CAS No. 5600-21-5 ] {[proInfo.proName]}

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Chemical Structure| 5600-21-5
Chemical Structure| 5600-21-5
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Product Details of [ 5600-21-5 ]

CAS No. :5600-21-5 MDL No. :MFCD00006091
Formula : C5H6ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :NPTGVVKPLWFPPX-UHFFFAOYSA-N
M.W :143.57 Pubchem ID :21810
Synonyms :

Calculated chemistry of [ 5600-21-5 ]

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 : 1.0
Molar Refractivity : 36.41
TPSA : 51.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.99
Solubility : 1.46 mg/ml ; 0.0102 mol/l
Class : Very soluble
Log S (Ali) : -1.9
Solubility : 1.79 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.27
Solubility : 0.766 mg/ml ; 0.00533 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 5600-21-5 ]

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 [ 5600-21-5 ]

* 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 [ 5600-21-5 ]
  • Downstream synthetic route of [ 5600-21-5 ]

[ 5600-21-5 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 3977-29-5 ]
  • [ 5600-21-5 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 43, p. 5921 - 5934
[2] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 343 - 348
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2429 - 2439
[4] Bioorganic Chemistry, 2018, vol. 78, p. 258 - 268
  • 2
  • [ 3977-29-5 ]
  • [ 5600-21-5 ]
YieldReaction ConditionsOperation in experiment
54% Reflux Amixture of 6 g of isocytosine IV and 35 mL of freshlydistilled phosphorus oxychloride was refluxed till themixture became homogeneous, then the excess of thechlorinating agent was removed in a vacuum. Forcooling, the residue was mixed with ice and treatedwith 25percent aqueous ammonia to 8. The formedsuspension was filtered, the precipitate was washedwith water, crystallized from 50percent ethanol, and dried toa constant mass. Yield 3.7 g (54percent), mp 188° (mp182–183° [7]), Rf 0.79 (D). Found, percent: 41.74;4.05; N 29.35. C5H6ClN3. Calculated, percent: 41.83;4.21; N 29.27.
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 1, p. 79 - 87[2] Zhurnal Obshchei Khimii, 2015, vol. 85, # 1, p. 79 - 87,9
  • 3
  • [ 22727-18-0 ]
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Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1622
  • 4
  • [ 5424-21-5 ]
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  • [ 14394-60-6 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 2934[2] Chemische Berichte, 1902, vol. 35, p. 1570
[3] Chemische Berichte, 1899, vol. 32, p. 2934[4] Chemische Berichte, 1902, vol. 35, p. 1570
  • 5
  • [ 5424-21-5 ]
  • [ 5600-21-5 ]
Reference: [1] Journal of the Chemical Society, 1951, p. 1004,1015[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84
  • 6
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  • [ 7664-41-7 ]
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  • [ 14394-60-6 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 2934[2] Chemische Berichte, 1902, vol. 35, p. 1570
  • 7
  • [ 3977-29-5 ]
  • [ 10025-87-3 ]
  • [ 5600-21-5 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 2934[2] Chemische Berichte, 1902, vol. 35, p. 1570
  • 8
  • [ 5424-21-5 ]
  • [ 5600-21-5 ]
  • [ 14394-60-6 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 2934[2] Chemische Berichte, 1902, vol. 35, p. 1570
[3] Chemische Berichte, 1899, vol. 32, p. 2934[4] Chemische Berichte, 1902, vol. 35, p. 1570
  • 9
  • [ 5424-21-5 ]
  • [ 7664-41-7 ]
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  • [ 14394-60-6 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 2934[2] Chemische Berichte, 1902, vol. 35, p. 1570
  • 10
  • [ 5600-21-5 ]
  • [ 1791-73-7 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 1242
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 940 - 950
[3] Patent: US5521192, 1996, A,
[4] Patent: US5622954, 1997, A,
  • 11
  • [ 5600-21-5 ]
  • [ 1791-73-7 ]
Reference: [1] Patent: US4083841, 1978, A,
  • 12
  • [ 5600-21-5 ]
  • [ 7664-41-7 ]
  • [ 1791-73-7 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 1242
  • 13
  • [ 5600-21-5 ]
  • [ 22536-64-7 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 598,600[2] Chem.Abstr., 1954, p. 9362
  • 14
  • [ 5600-21-5 ]
  • [ 124-41-4 ]
  • [ 7749-47-5 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 598,600[2] Chem.Abstr., 1954, p. 9362
[3] Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 291,297
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 3072,3075
  • 15
  • [ 5600-21-5 ]
  • [ 70-23-5 ]
  • [ 7749-47-5 ]
  • [ 134044-64-7 ]
  • [ 156756-45-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 1994, vol. 29, # 4, p. 279 - 286
  • 16
  • [ 67-56-1 ]
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  • [ 70-23-5 ]
  • [ 7749-47-5 ]
  • [ 134044-64-7 ]
  • [ 156756-45-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 1994, vol. 29, # 4, p. 279 - 286
  • 17
  • [ 5600-21-5 ]
  • [ 6314-12-1 ]
YieldReaction ConditionsOperation in experiment
97% With bromine In dichloromethane at 20℃; for 1.5 h; Example 61. 5-Bromo-4-chloro-6-methylpyrimidin-2-amine; <n="64"/>To a mixture of the 2-amino-4-chloro-6-methyl pyrimidine (5.00 g, 34.8 mmol) in dichloromethane (240 ml.) was added bromine (1.88 ml_, 36.6 mmol). The resulting suspension was stirred at room temperature for 1.5 hours. The mixture was diluted with dichloromethane (1.3 L) and washed with saturated sodium bicarbonate (2 x 200 mL) and brine (200 ml_), dried (MgSO4), filtered and concentrated to afford 5-bromo-4-chloro-6-methylpyrimidin-2-amine (7.5 g, 97percent). LCMS (M+H): 223 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.54 (s, 3 H) 5.10 (s, 2 H)
70% With N-Bromosuccinimide In N,N-dimethyl-formamide for 12 h; To a solution of compound 2 (143.6 mg, 1 mmol) in anhydrous DMF (5 mL) was added NIS (225 mg, 1 mmol), and the reaction mixture was stirred for 12 h.
The reaction mixture was diluted with water and extracted with EtOAc (3*30 mL).
The combined organic layer was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (40percent EtOAc/hexanes) to obtain the compound 3 as a white solid (210 mg, 78percent).
1H NMR (500 MHz, MeOD) δ 2.55 (s, 3H).
13C NMR (126 MHz, MeOD) δ 173.86, 165.51, 163.76, 79.58, 30.16. MS (ESI-TOF) for C5H5ClIN3 [M+H]+ calculated 269.9289, found 269.9350.
58% With bromine In dichloromethane at 20℃; for 2 h; To a mixture of compound 5a (100 g, 696 mmol) in DCM (1 L) was added liquid bromine (37.5 mL, 731 mmol) and the mixture was stirred at rt for 2 h. The mixture was washed with saturated Na2S2O3 solution and brine, dried over Na2SO4, filtered and concentrated. The residue was recrystallized from EtOAc to afford 5b as a yellow solid (90 g, 58percent yield). 1H NMR (400 MHz, DMSO-d6) δ 7.19 (br s, 2H), 2.40 (s, 3H). MS (ESI+) m/z 400.7 [M + H]+.MS (ESI+) m/z 222.0 [M + H]+
Reference: [1] Patent: WO2008/32162, 2008, A1, . Location in patent: Page/Page column 62-63
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5098 - 5103
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 17, p. 8082 - 8093
[4] Patent: US2018/215720, 2018, A1, . Location in patent: Paragraph 0057; 0059; 0074
[5] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 3, p. 637 - 646
[6] Patent: US2014/38991, 2014, A1, . Location in patent: Paragraph 0172; 0173; 0174
  • 18
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  • [ 99586-66-0 ]
Reference: [1] Patent: US2013/53362, 2013, A1,
  • 19
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  • [ 934493-76-2 ]
Reference: [1] Patent: WO2008/127678, 2008, A1,
  • 20
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  • [ 1020149-73-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1631 - 1635
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1631 - 1635
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 701 - 713
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