Phosphorus oxychloride → 5-Bromo-4-chloro-7-methyl-8-nitroquinazoline

HRID 1469761ノート

反応式

HRID 1469761 の反応式
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-:15])=[O:14])=[C:8]2[C:3]=1[C:4](=O)[NH:5][CH:6]=[N:7]2.O=P(Cl)(Cl)[Cl:19]>>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-:15])=[O:14])=[C:8]2[C:3]=1[C:4]([Cl:19])=[N:5][CH:6]=[N:7]2

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 1363368225-bromo-7-methyl-8-nitroquinazolin-4(3H)-one

生成物 1

HCID 866922505-Bromo-4-chloro-7-methyl-8-nitroquinazoline

実験手順

A solution of 5-bromo-7-methyl-8-nitroquinazolin-4(3H)-one (200 mg, 0.71 mmol) in POCl3 (4 mL) was heated at reflux for 4 h. Then the reaction mixture was concentrated and the residue was co-evaporated with toluene and dried to afford 5-bromo-4-chloro-7-methyl-8-nitroquinazoline which was dissolved in THF (5 mL). Then the solution was treated with 3-(trifluoromethyl)aniline (457 mg, 2.84 mmol) and DIPEA (458 mg, 3.55 mmol) at 0° C. and the reaction mixture was stirred at rt for 12 h before it was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered, concentrated and purified by column chromatography to afford 215 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.36 (s, 1H), 9.15 (s, 1H), 8.72 (s, 1H), 8.29 (s, 1H), 8.23 (d, J=8.4 Hz, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 2.47 (s, 3H); MS (m/z): 427.17 (M)+.

後処理

  1. temperatureat reflux for 4 h
  2. concentrationThen the reaction mixture was concentrated
  3. customdried

出典と根拠

ORDレコード
ord-3d1a00c0bb844278ab22b6fbe0857d90
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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