Ammonia → 8-Bromo-2-chloroquinazolin-4-amine

HRID 1056370노트

반응식

HRID 1056370 반응식
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[C:7]2Cl.[OH-].[NH4+:15].N>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[C:7]2[NH2:15]

참가 물질

6

반응물 3

HCID 222Ammonia2회HCID 14923Ammonium HydroxideHCID 137858748-Bromo-2,4-dichloroquinazoline

생성물 1

HCID 137858778-Bromo-2-chloroquinazolin-4-amine수율 68%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To a slurry of 8-bromo-2,4-dichloroquinazoline (407b; 0.50 g, 1.80 mmol) in 2 mL THF at 0° C. was added ammonium hydroxide, 28% ammonia in water (3.25 mL, 23.39 mmol). The reaction was sealed and the ice/water bath was removed. The heterogeneous reaction was stirred rapidly. In the morning starting material was still evident. 2 mL THF and 1 mL 28% ammonia in water were added and the reaction became homogeneous. After 1 h, reaction was checked and judged complete. The reaction was partitioned between water and DCM. The layers were separated and the aqueous layer was filtered through Celite and the filtrate was extracted 2×DCM and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-chloroquinazolin-4-amine (0.318 g, 1.23 mmol, 68% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.52 (2H, br. s.), 8.24 (1H, d, J=8.4 Hz), 8.14 (1H, d, J=7.6 Hz), 7.42 (1H, t, J=7.9 Hz). m/z (ESI, +ve ion) 257.9/259.9 (M+H)+.

후처리

  1. customThe reaction was sealed
  2. customthe ice/water bath was removed
  3. customThe heterogeneous reaction
  4. customreaction
  5. customThe reaction was partitioned between water and DCM
  6. customThe layers were separated
  7. filtrationthe aqueous layer was filtered through Celite
  8. extractionthe filtrate was extracted 2×DCM
  9. dry with materialthe combined organics were dried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f3f7dce0c28d4125a338e7d89bc634d6
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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