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

HRID 1056370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056370
[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]

Komponenten

6

Edukt 3

HCID 222Ammonia2×HCID 14923Ammonium HydroxideHCID 137858748-Bromo-2,4-dichloroquinazoline

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f3f7dce0c28d4125a338e7d89bc634d6
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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