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[ CAS No. 956100-62-2 ]

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Chemical Structure| 956100-62-2
Chemical Structure| 956100-62-2
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Product Details of [ 956100-62-2 ]

CAS No. :956100-62-2 MDL No. :MFCD11858275
Formula : C8H5BrClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :258.50 g/mol Pubchem ID :13785877
Synonyms :

Safety of [ 956100-62-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 956100-62-2 ]

  • Upstream synthesis route of [ 956100-62-2 ]
  • Downstream synthetic route of [ 956100-62-2 ]

[ 956100-62-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 956100-62-2 ]
  • [ 956100-63-3 ]
YieldReaction ConditionsOperation in experiment
67% With isopentyl nitrite In tetrahydrofuran at 60℃; for 8.67 h; To a stirred mixture of 8-bromo-2-chloroquinazolin-4-amine (12.93 g, 50 mmol) in THF (500 mL) was added isoamyl nitrite (23.43 g, 200 mmol) over 3 hours and 40 mins at 6O0C. The mixture was stirred for another 5 hours. TLC (PE:EA,1 :1) showed reaction complete. After cooling to room temperature, the <n="83"/>solvent was stripped and the residue was taken into DCM (300 mL). The organic layer was washed with brine (100 mL), water (100 mL), then dried over anhydrous Na2SO4 and purified by chromatography (DCM:PE, 1:1) to give the title compound as a yellow solid ( 8.21 g, 67percent). 1 HNMR (DMSOd6, 400 MHz): δ 9.66 (s, 1 H), 8.45 (dd, J = 0.8, 7.6 Hz, 1 H), 8.26 (dd, J = 0.8, 8.0 Hz, 7.73 (dd, J = 7.6, 8.0 Hz, 1 H).
56% With tert-amyl nitrite In tetrahydrofuran at 70℃; for 18 h; Compound 19-d (1.5 g, 5.84 mmol) was dissolved in tetrahydrofuran (20 mL) and tertamyl nitrite (2.7 g, 23.36mmol) was added. The reaction mixture was heated at 70°C for 18 hours and the reaction mixture was concentratedunder reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: dichloromethane= 3: 1) to deliver a pale yellow solid 19-c (0.79 g, yield: 56percent). LC-MS (ESI): m/z = 243 [M+H]+.
23% With isopentyl nitrite In tetrahydrofuran at 70℃; for 12 h; To a solution of 8-bromo-2-chloroquinazolin-4-amine (7.1 g, 27 mmol, 1 eq.) in THF (80 mL) at 70 °C was added isopentyl nitrite (14 mL, 108 mmol, 4 eq.) dropwise. The resulting mixture was stirred at 70 °C for 12 h, then cooled to r.t. and concentrated. The resulting residue was purified via column chromatography (PE/EA=5: 1, v/v) to afford 8-bromo-2-chloroquinazoline
0.79 g With tert-amyl nitrite In tetrahydrofuran at 70℃; for 18 h; Compound 44-d (1.5 g, 5.84 mmol) was dissolved in tetrahydrofuran (20 mL) and tert-amyl nitrite (2.7 g, 23.36 mmol) was added. The reaction mixture was heated at 70° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (petroleum ether: dichloromethane=3:1) to give 44-c as a light yellow solid (0.79 g, yield 56percent). LC-MS (ESI): m/z=243[M+H]+.

Reference: [1] Patent: WO2007/125405, 2007, A2, . Location in patent: Page/Page column 25; 81-82
[2] Patent: EP3287463, 2018, A1, . Location in patent: Paragraph 0191; 0195
[3] Patent: WO2015/27222, 2015, A2, . Location in patent: Paragraph 0216
[4] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0484-0485
  • 2
  • [ 331647-05-3 ]
  • [ 956100-62-2 ]
YieldReaction ConditionsOperation in experiment
100% With ammonia In methanol; dichloromethane at 20℃; for 16 h; Compound 19-e (1.2 g, 4.35 mmol) was dissolved in dichloromethane (5 mL) and then ammonia (50 mL, 7 Min methanol), was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixturewas concentrated under reduced pressure and the residue was added to water (50 mL), a solid was precipitated andfiltered. The filter cake was washed with water (50 mL) and dried in vacuo to deliver a yellow solid 19-d (1.5 g, yield:100percent). This product was used directly for the next step without further purification
99% With ammonia In dichloromethane at 20℃; 8-bromo-2,4-dichloroquinazoline (13.90 g, 50 mmol) was dissolved in DCM (60 mL) and ammonia was bubbled through the reaction solution with stirring overnight at room temperature. A suspension was formed, and the precipitate was collected by filtration to give crude title compound as a white solid (12.93 g, 99percent).
83.5% With ammonium hydroxide In tetrahydrofuran at 0℃; for 0.5 h; To a solution of ammonia hydroxide (25 mL, 330 mmol, 10 eq.) in THF (50 mL) cooled to 0 °C was added a solution of 8-bromo-2,4-dichloroquinazoline (9.1 g, 32.7 mmol, 1 eq.) in THF (50 mL). The mixture was stirred at 0 °C for 30 min, then diluted with EA (100 mL), washed with brine, dried over anhydrous Na2S04and concentrated. The resulting residue was purified via column chromatography (PE/EA=10: 1, v/v) to afford 8-bromo-2- chloroquinazolin-4-amine as a yellow solid (7.1 g, 83.5percent yield).
83.5% With ammonium hydroxide In tetrahydrofuran at 0℃; for 0.5 h; [0288] To a solution of ammonia hydroxide (25 mL, 330 mmol, 10 eq.) in THF (50 mL) cooled to 0 °C was added a solution of 8-bromo-2,4-dichloroquinazoline (9.1 g, 32.7 mmol, 1 eq.) in THF (50 mL). The mixture was stirred at 0 °C for 30 mm, then diluted with EA (100 mL), washed with brine, dried over anhydrous Na2504 and concentrated. The resulting residue was purified via column chromatography (PE/EA=10: 1, v/v) to afford 8-bromo-2- chloroquinazolin-4-amine as a yellow solid (7.1 g, 83.5percent yield).

Reference: [1] Patent: EP3287463, 2018, A1, . Location in patent: Paragraph 0191; 0194
[2] Patent: WO2007/125405, 2007, A2, . Location in patent: Page/Page column 25; 81
[3] Patent: WO2015/27222, 2015, A2, . Location in patent: Paragraph 0215
[4] Patent: WO2016/133935, 2016, A1, . Location in patent: Paragraph 0288
[5] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0482-0483
  • 3
  • [ 20776-51-6 ]
  • [ 956100-62-2 ]
Reference: [1] Patent: WO2015/27222, 2015, A2,
[2] Patent: WO2016/133935, 2016, A1,
[3] Patent: EP3287463, 2018, A1,
[4] Patent: US2018/208604, 2018, A1,
  • 4
  • [ 331646-99-2 ]
  • [ 956100-62-2 ]
Reference: [1] Patent: WO2015/27222, 2015, A2,
[2] Patent: WO2016/133935, 2016, A1,
  • 5
  • [ 331646-99-2 ]
  • [ 956100-62-2 ]
Reference: [1] Patent: EP3287463, 2018, A1,
[2] Patent: US2018/208604, 2018, A1,
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