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[ CAS No. 14527-26-5 ] {[proInfo.proName]}

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Chemical Structure| 14527-26-5
Chemical Structure| 14527-26-5
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Product Details of [ 14527-26-5 ]

CAS No. :14527-26-5 MDL No. :MFCD00135509
Formula : C2H8N2O4S2 Boiling Point : -
Linear Structure Formula :- InChI Key :NNBBQNFHCVVQHZ-UHFFFAOYSA-N
M.W : 188.23 Pubchem ID :75270
Synonyms :

Safety of [ 14527-26-5 ]

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 [ 14527-26-5 ]

* 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 [ 14527-26-5 ]
  • Downstream synthetic route of [ 14527-26-5 ]

[ 14527-26-5 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 14527-26-5 ]
  • [ 141-97-9 ]
  • [ 6328-58-1 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium carbonate In water at 20℃;
Stage #2: Alkaline aqueous solution
Intermediate 1; 2-amino-8-ethyl-4-methyl-6-(lJϊ-pyrazol-3-yl)pyrido[2,3-d]pyrimidm-7(8Jff)-one; [00200] To a solution of 2-methyl-2-thiopseudourea sulfate (Aldrich, 58.74 g, 0.422 mol) in water (1000 niL) were added sodium carbonate (81.44 g, 0.768 mol) and ethyl acetoacetate (50 g, 0.384 mol) at room temperature. The reaction mixture was stirred overnight. After neutralizing to pH = 8, the solid was collected through filtration followed by drying under vacuum overnight to afford 6-methyl-2-(methylthio)pyrimidin-4(3H)-one (57.2 g, 95percent yield) of product. 1H NMR (400 MHz, DMSO-d6): δ 12.47 (bs, IH), 5.96 (bs, IH), 2.47(s, 3H), 2.17 (s, 3H).
Reference: [1] Patent: WO2007/44698, 2007, A1, . Location in patent: Page/Page column 62
  • 2
  • [ 87-56-9 ]
  • [ 14527-26-5 ]
  • [ 61727-33-1 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 1, p. 153 - 157
  • 3
  • [ 488-11-9 ]
  • [ 14527-26-5 ]
  • [ 50593-92-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2215 - 2226
  • 4
  • [ 85302-07-4 ]
  • [ 14527-26-5 ]
  • [ 21599-35-9 ]
YieldReaction ConditionsOperation in experiment
90% With sodium carbonate In 1,4-dioxane for 8 h; Reflux A mixture of compounds 2 (20 g, 120 mmol), sodium carbonate (15.2 g, 144 mmol) and the S-methyllisothiourea sulfate (27.11 g, 144 mmol) was added in 1,4-dioxane (450 mL). The reaction solution was refluxed for 8 h. After completion of the reaction as monitored by TLC, the mixture was cooled to room temperature. Water was added drop by drop, giving a precipitate, which was collected, and purified by flash column chromatography (petroleum ether/ethyl acetate, 8:1 v/v) to afford pure product 9. White solid. Yield: 90percent; 1H NMR (400 MHz, DMSO) δ: 9.19 (s, 1H, -CH), 3.15 (t, J = 6.2 Hz, 2H, -CH2), 2.92 (s, 3H, -SCH3), 2.74 (t, J = 6.2 Hz, 2H, -CH2), 2.17 (m, 2H, -CH2); 13C NMR (100 MHz, DMSO) δ: 196.00, 175.80, 166.44, 159.63, 121.32, 55.75, 38.18, 31.91, 21.09; HRMS calculated for C9H10N2OS 195.0592 [M+H]+, found 195.0581.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 20, p. 3385 - 3390
  • 5
  • [ 14527-26-5 ]
  • [ 21599-35-9 ]
YieldReaction ConditionsOperation in experiment
60.2% for 2 h; Reflux To a solution of 2-[(dimethylamino)methyl]-cyclohexane-1,3-dione (10.3 g, 46.0 mmol) in acetic acid (65 ml), S-methylisothiourea sulfate was added dropwise (2.44 ml, 46.0 mmol) and sodium carbonate (6.81 g, 83.4 mmol),The reaction was heated to reflux for 2 h.Add water (100 ml) and ethyl acetate (100 ml), and separate.The aqueous layer was extracted with ethyl acetate (100×2 mL).After drying over anhydrous magnesium sulfate, suction filtered, and the filtrate was evaporated.The residue is via ethanol:Water (1:1, 50ml) recrystallized,A yellow solid was obtained (6.85 g, 60.2percent).
Reference: [1] Patent: CN108484606, 2018, A, . Location in patent: Paragraph 0044; 0045; 0046
  • 6
  • [ 14527-26-5 ]
  • [ 105-53-3 ]
  • [ 1979-98-2 ]
Reference: [1] Synthetic Communications, 2018, vol. 48, # 6, p. 714 - 720
  • 7
  • [ 603-67-8 ]
  • [ 14527-26-5 ]
  • [ 1979-97-1 ]
Reference: [1] Synthetic Communications, 2018, vol. 48, # 6, p. 714 - 720
  • 8
  • [ 42466-67-1 ]
  • [ 14527-26-5 ]
  • [ 89487-99-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 30 - 38
  • 9
  • [ 14527-26-5 ]
  • [ 94-05-3 ]
  • [ 89487-99-0 ]
Reference: [1] Patent: US2003/158218, 2003, A1,
  • 10
  • [ 14527-26-5 ]
  • [ 38275-41-1 ]
Reference: [1] Patent: WO2006/88949, 2006, A1, . Location in patent: Page/Page column 91
  • 11
  • [ 14527-26-5 ]
  • [ 38275-41-1 ]
Reference: [1] Synthesis, 2002, # 6, p. 720 - 722
  • 12
  • [ 14527-26-5 ]
  • [ 73781-88-1 ]
Reference: [1] Farmaco, 1993, vol. 48, # 3, p. 335 - 355
  • 13
  • [ 14527-26-5 ]
  • [ 92385-43-8 ]
  • [ 73781-88-1 ]
Reference: [1] Journal of Chemical Research, 2007, # 8, p. 490 - 493
  • 14
  • [ 14527-26-5 ]
  • [ 110-60-1 ]
  • [ 306-60-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 3071
  • 15
  • [ 14527-26-5 ]
  • [ 2009-81-6 ]
  • [ 90905-31-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1281 - 1285
  • 16
  • [ 14527-26-5 ]
  • [ 110-60-1 ]
  • [ 2482-00-0 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2510
  • 17
  • [ 24424-99-5 ]
  • [ 14527-26-5 ]
  • [ 173998-77-1 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In dichloromethane at 0℃; for 6.33333 h; To a rapidly stirred suspension of S-Methylisothiourea hemisulfate (60.8 g, 0.437 mol) in CH2Cl2 (600 mL) was added 2N NaOH (300 mL, 0.6 mol).
This mixture was cooled to 0° C. on an ice bath, and a solution of di-tert-butyl dicarbonate (43.2 g, 0.198 mol) was added dropwise over 6 h.
Upon completion of the addition, the mixture was stirred an additional 20 min, diluted with IL of CH2Cl2 and the phases were separated.
The organic portion was washed with water (2*500 ml) and dried over Na2SO4.
Filtration and concentration provided the desired N-Boc-S-methylisothiourea as a white solid (35.5 g, 0.187 mol, 94percent yield based on Boc2O).
Reference: [1] Patent: US2007/232679, 2007, A1, . Location in patent: Page/Page column 8-9
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