Acetic Acid → 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amine

HRID 1520833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520833
C(O)(=O)C.[N+:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[N:15]2)=[N:12][CH:13]=1)([O-])=O>CO.C(OCC)(=O)C.[Fe]>[F:22][C:19]([F:20])([F:21])[C:17]1[CH:16]=[N:15][N:14]([C:11]2[N:12]=[CH:13][C:8]([NH2:5])=[CH:9][N:10]=2)[CH:18]=1

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 681573265-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine

Produkt 1

HCID 641756422-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Glacial acetic acid (2.78 g, 46.3 mmol) was slowly added to a solution of 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine (1.5 g, 5.8 mmol) and iron powder (1.94 g, 34.7 mmol) in methanol (30 mL). The reaction was stirred at room temperature for 3 hours. The reaction was then diluted with ethyl acetate (50 mL) and filtered through Celite. The filtrate was neutralized with saturated aqueous potassium carbonate. The organic layer was separated and washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amine (850 mg, 64%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 8.68 (s, 1H), 8.16 (s, 2H), 7.87 (s, 1H), 3.82 (s, 2H).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bd3a2fdd66a8403c8ba9193cd3eabc9d
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073871B2

Notizen zur Reaktion

Wird geladen…