Triethylamine → Tert-butyl 3-(6-chloropyrimidin-4-ylamino)phenylcarbamate

HRID 404767

Reaktionsgleichung

Reaktionsgleichung von HRID 404767
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1.C(N(CC)CC)C>C(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Produkt 1

HCID 57708283Tert-butyl 3-(6-chloropyrimidin-4-ylamino)phenylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4,6-Dichloropyrimidine (1.5 g, 10 mmol), tert-butyl 3-aminophenylcarbamate (2.1 g, 10 mmol) and triethylamine (2.2 g, 20 mmol) were mixed in ethanol (20 mL), heated at 80° C. for 16 hr. The reaction mixture was cooled to RT and solvent was removed in vacuo. The gummy crude product was mixed with 20 mL of DCM and was stirred at RT to give an off-white solid, which was filtered and dried under vacuum (1.6 g, 5 mmol). MS (m/z): MH+=321, 323.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. customsolvent was removed in vacuo
  3. additionThe gummy crude product was mixed with 20 mL of DCM
  4. customto give an off-white solid, which
  5. filtrationwas filtered
  6. customdried under vacuum (1.6 g, 5 mmol)

Quellen und Nachweise

ORD-Eintrag
ord-224bfa23e9db4f3aa6f1aca4bfb637f7
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748606B2

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