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

HRID 1055813노트

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HRID 1055813 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-da4be8cb3f764e41a091d988a5779283
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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