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[ CAS No. 153436-68-1 ]

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Chemical Structure| 153436-68-1
Chemical Structure| 153436-68-1
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Product Details of [ 153436-68-1 ]

CAS No. :153436-68-1 MDL No. :MFCD09701986
Formula : C9H6BrClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :257.51 g/mol Pubchem ID :21941937
Synonyms :

Safety of [ 153436-68-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331-H341 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 153436-68-1 ]

  • Downstream synthetic route of [ 153436-68-1 ]

[ 153436-68-1 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 58421-79-7 ]
  • [ 153436-68-1 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; A. 6-Bromomethyl-4-chloro-quinazoline. A flask containing 4-Chloro-6-methylquinazoline (0.91 g, 5.09 mmol), NBS (0.95 g, 5.35 mmol), benzoyl peroxide 70% (0.09 g, 0.2545 mmol) and carbon tetrachloride (25 mL) is refluxed at 80 C. for 20 h. The solution is cooled to RT, filtered and concentrated. Purification by flash chromatography (7.5% EtOAc/hexanes) yields the title compound as a white solid (0.62 g, 2.42 mmol). 1H NMR (CDCl3, 300 MHz) 9.06 (s, 1H), 8.25 (s, 1H), 8.07 (d, 1H), 8.00 (d, 1H), 4.67 (s, 2H).
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; A. 6-Bromomethyl-4-chloro-quinazoline A flask containing 4-Chloro-6-methylquinazoline (0.91 g, 5.09 mmol), NBS (0.95 g, 5.35 mmol), benzoyl peroxide 70% (0.09 g, 0.2545 mmol) and carbon tetrachloride (25 mL) is refluxed at 80 C. for 20 h. The solution is cooled to RT, filtered and concentrated. Purification by flash chromatography (7.5% EtOAc/hexanes) yields the title compound as a white solid (0.62 g, 2.42 mmol). 1H NMR (CDCl3, 300 MHz) 9.06(s, 1H), 8.25(s, 1H), 8.07(d, 1H), 8.00(d, 1H), 4.67(s, 2H).
  • 2
  • [ 153436-68-1 ]
  • [ 108-44-1 ]
  • [ 195457-65-9 ]
YieldReaction ConditionsOperation in experiment
32% In diethyl ether; N,N-dimethyl-formamide; EXAMPLE 35 3-Methylaniline (0.123 g) was added dropwise to a stirred solution of <strong>[153436-68-1]6-bromomethyl-4-chloroquinazoline</strong> (0.3 g) in DMF (3 ml). The mixture was stirred at ambient temperature for 2 hours. Diethyl ether (10 ml) was added and the precipitate was isolated. There was thus obtained 6-bromomethyl-4-(3'-methylanilino)quinazoline in 32% yield, m.p. >260 C. (decomposes); NMR Spectrum: (CD3 SOCD3) 2.37 (s, 3H), 4.98 (s, 2H), 7.17 (d, 1H), 7.39 (t, 1H), 7.53 (m, 2H), 7.95 (d, 1H), 8.15 (m, 1H), 8.93 (s, 1H), 8.96 (d, 1H), 11.59 (broad s, 1H); Elemental Analysis: Found C, 56.5; H, 4.6; N, 12.3; C16 H14 BrN3. 0.25HCl requires C, 56.9; H, 4.3; N, 12.4%.
  • 3
  • 4-chloro-6-methylquinzoline [ No CAS ]
  • 4-chloro-6-dibromomethylquinazoline [ No CAS ]
  • [ 153436-68-1 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; g. The product gave the following analytical data: Found C, 41.4; H, 3.4; N, 9.1; C16 H13 BrN3. HCl. 1.1H2 O requires C, 41.4; H, 3.5; N, 9.1; and the following characteristic NMR data: (CD3 SOCD3) 2.38 (s, 3H), 7.18 (d, 1H), 7.40 (t, 1H), 7.49 (m, 2H), 7.51 (s, 1H), 7.94 (d, 1H), 8.29 (m, 1H), 8.91 (s, 1H), 9.10 (d, 1H), 11.7 (s, 1H). The 4-chloro-6-dibromomethylquinazoline used as a starting material was obtained as follows: A mixture of 4-chloro-6-methylquinzoline (7.3 g) [obtained by the reaction 6-methyl-4-oxo-3,4-dihydroquinazoline (European Patent Application No. 86304148.9) with thionyl chloride], N-bromosuccinimide (7.32 g) dibenzoyl peroxide (0.1 g) and carbon tetrachloride (200 ml) was stirred and heated to reflux for 6 hours. The mixture was evaporated and the residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There were thus obtained in turn 4-chloro-6-dibromomethylquinazoline (0.5 g) and 6-bromomethyl-4-chloroquinazoline (4 g).
YieldReaction ConditionsOperation in experiment
C. 6-Bromomethyl-4-chloro-quinazoline The title compound is prepared as described in EXAMPLE 1, Part F substituting 4-chloro-6-methyl-quinazoline for 1-chloro-7-methylisoquinoline. The crude product is purified by column chromatography eluding with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes to give the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) delta9.08 (s, 1H), 8.23 (s, 1H), 8.00 (dd, 2H), 4.68 (s, 2H).
  • 5
  • [ 153436-68-1 ]
  • [ 209286-53-3 ]
  • [ 209286-54-4 ]
YieldReaction ConditionsOperation in experiment
With LiN(SiMe3)2; ammonium chloride; In tetrahydrofuran; ethyl acetate; F. 7-Methoxynaphthalene-2-sulfonic acid [1-(4-chloro-quinazolin-6-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-methyl amide To a solution of 7-methoxynaphthalene-2-sulfonic acid methyl-(2-oxopyrrolidin-3-(S)-yl)-amide (0.35 g, 1.04 mmol) in THF (7 mL) at 0 C. is added LiN(SiMe3)2 (1 mL, 1 mmol, 1 M solution in THF). The solution is stirred at 0 C. for 40 minutes. After this time, <strong>[153436-68-1]6-bromomethyl-4-chloro-quinazoline</strong> (0.24 g, 0.94 mmol) is added. The resulting solution is stirred for 4 hours. The reaction is quenched by the addition of a saturated NH4Cl solution. The solution is diluted with EtOAc and water. The layers are separated. The organic layer is washed with water and brine. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluding with a gradient of 20% EtOAc/CH2Cl2 to 40% EtOAc/CH2Cl2 to give the title compound (0.25 g, 0.49 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) delta9.03 (s, 1H), 8.40 (s, 1H), 8.03 (m, 2H), 7.89 (d, 1H), 7.81 (m, 3H), 7.28 (m, 2H), 5.00 (m, 1H), 4.75 (AB, 1H), 4.50 (AB, 1H), 3.92 (s, 3H), 3.22 (m, 2H), 2.87 (s, 3H), 2.38 (m, 1H), 2.03 (m, 1H). FAB MS, [M+H]+=511.
  • 6
  • [ 2941-78-8 ]
  • [ 153436-68-1 ]
  • 7
  • [ 19181-53-4 ]
  • [ 153436-68-1 ]
  • 8
  • [ 153436-68-1 ]
  • [ 1259017-75-8 ]
  • 9
  • [ 153436-68-1 ]
  • [ 1259017-77-0 ]
  • 10
  • [ 153436-68-1 ]
  • [ 1259017-78-1 ]
  • 11
  • [ 153436-68-1 ]
  • C22H18ClFN4O [ No CAS ]
  • 12
  • [ 153436-68-1 ]
  • C15H12ClFN4 [ No CAS ]
  • 13
  • [ 153436-68-1 ]
  • C15H13BrN4 [ No CAS ]
  • 14
  • [ 153436-68-1 ]
  • [ 1259017-58-7 ]
  • 15
  • [ 153436-68-1 ]
  • [ 1259017-59-8 ]
  • 16
  • [ 153436-68-1 ]
  • [ 1259017-60-1 ]
  • 17
  • [ 153436-68-1 ]
  • [ 1259017-61-2 ]
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