Tert-Butylamine → 8-bromo-N2-(tert-butyl)quinazoline-2,4-diamine

HRID 1056371노트

반응식

HRID 1056371 반응식
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[C:7]2[NH2:13].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])[N:8]=[C:7]2[NH2:13]

참가 물질

4

반응물 2

HCID 6385Tert-ButylamineHCID 137858778-Bromo-2-chloroquinazolin-4-amine

생성물 1

HCID 897822178-bromo-N2-(tert-butyl)quinazoline-2,4-diamine수율 106.9%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A microwave vial was charged with 8-bromo-2-chloroquinazolin-4-amine (484a; 0.109 g, 0.422 mmol) and tert-butylamine (Aldrich; 1.33 mL, 12.65 mmol). The slurry was heated to 120° C. in a biotage initiator microwave for 30 min. 0.5 mL NMP was added to give a solution and the reaction was heated to 120° C. in a biotage initiator microwave for 30 min. The reaction was heated to 150° C. in a biotage initiator microwave for 30 min. The reaction was heated to 160° C. in a biotage initiator microwave for 30 min and then was heated to 170° C. in a biotage initiator microwave for 30 min. The reaction was partitioned between water and EtOAc. The organic layer was washed with water 2 times, saturated aqueous NaCl once, and the organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-N2-(tert-butyl)quinazoline-2,4-diamine (0.133 g, 0.451 mmol, quant. yield) as a brown foam: 1H NMR (400 MHz, CDCl3) δ ppm 7.87 (1H, dd, J=7.5, 1.3 Hz), 7.48 (1H, d, J=7.8 Hz), 6.92 (1H, t, J=7.8 Hz), 5.27 (2H, br. s.), 5.02 (1H, br. s.), 1.55 (9H, s). m/z (ESI, +ve ion) 295.0/297.0 (M+H)+.

후처리

  1. customto give a solution
  2. temperaturethe reaction was heated to 120° C. in a biotage initiator microwave for 30 min
  3. temperatureThe reaction was heated to 150° C. in a biotage initiator microwave for 30 min
  4. temperatureThe reaction was heated to 160° C. in a biotage initiator microwave for 30 min
  5. temperaturewas heated to 170° C. in a biotage initiator microwave for 30 min
  6. customThe reaction was partitioned between water and EtOAc
  7. washThe organic layer was washed with water 2 times, saturated aqueous NaCl once
  8. dry with materialthe organics were dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a288786d1b554872a884fb9c387d5876
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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