Benzoyl Peroxide → 2-(1-Bromomethyl)quinazoline

HRID 1804640Notes

Reaction equation

HRID 1804640 reaction equation
[CH2:1]([C:3]1[N:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)C.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:20][CH2:1][C:3]1[N:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 3080902N-(10)-Ethylquinazoline

Product 1

HCID 218511882-(1-Bromomethyl)quinazolineYield 12.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the title compound from Step B (1.39 g 8.79 mmol) in chloroform (50 ml) was added NBS (1.56 g, 8.79 mmol) and benzoyl peroxide (213 mg, 0.88 mmol) and the resulting mixture heated at reflux for 5 h. The mixture cooled and evaporated, the residue purified by MPLC (Biotage Horizon: FLASH 25+M) eluent: 100% Hexanes (90 ml), gradient rising from 100% Hexanes to 10% EtOAc in Hexanes (1200 ml) to afford the title compound 240 mg (11.5%) as a red oil. 1H NMR (CDCl3): 2.25 (d, J 6.9 Hz, 3H), 5.51 (q, J 6.9 Hz, 1H), 7.64 (m, 1H), 7.71 (m, 1H), 7.97 (m, 1H), 8.08 (d, J 8.6 Hz, 1H), 9.49 (s, 1H).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 5 h
  3. temperatureThe mixture cooled
  4. customevaporated
  5. customthe residue purified by MPLC (Biotage Horizon: FLASH 25+M) eluent

Sources & evidence

ORD record
ord-6927fa866c95457199e74c9152b5dce4
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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