Tert-Butylamine → 2-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one

HRID 1055813ノート

反応式

HRID 1055813 の反応式
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Cl[C:7]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[C:9](=[C:10]([I:19])[CH:11]=[CH:12][CH:13]=2)[N:8]=1>C1COCC1>[C:1]([NH:5][C:7]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[C:9](=[C:10]([I:19])[CH:11]=[CH:12][CH:13]=2)[N:8]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 6385Tert-ButylamineHCID 897821932-Chloro-8-iodo-3-methyl-quinazolin-4-one

生成物 1

HCID 897821382-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A heterogeneous mixture of tert-butylamine (22.83 mL, 217 mmol) and 2-chloro-8-iodo-3-methylquinazolin-4(3H)-one (700) (4.64 g, 14.48 mmol) in 2 mL of THF in a 100 mL RBF fitted with a reflux condenser was heated in an oil bath at 50° C. for 4 h. The reaction mixture was concentrated under reduced pressure and the brown solid was dissolved in 300 mL of EtOAc, washed sequentially with 10 mL of water, 10 mL of sat. NaHCO3 solution and 10 mL of brine. The organic solution was concentrated. The residue was purified on a silica gel column (25-55% EtOAc in hexanes) to afford 2-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one (4.64 g, 12.99 mmol, 90% yield) as a yellow crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.12 (1H, dd, J=7.5, 1.3 Hz), 7.93 (1H, dd, J=7.8, 1.2 Hz), 6.89 (1H, t, J=7.6 Hz), 6.02 (1H, s), 3.41 (3H, s), 1.60 (9H, s). m/z (ES, +ve) 358.1 (M+H)+.

後処理

  1. customRBF fitted with a reflux condenser
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe brown solid was dissolved in 300 mL of EtOAc
  4. washwashed sequentially with 10 mL of water, 10 mL of sat. NaHCO3 solution and 10 mL of brine
  5. concentrationThe organic solution was concentrated
  6. customThe residue was purified on a silica gel column (25-55% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-da4be8cb3f764e41a091d988a5779283
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

反応ノート

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