Water → 4-Chloro-2-amino-6-[1-(4-methylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidine

HRID 419220

Reaktionsgleichung

Reaktionsgleichung von HRID 419220
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.[NH2:16][C:17]1[N:22]=[C:21](Cl)[CH:20]=[C:19]([Cl:24])[N:18]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:24][C:19]1[CH:20]=[C:21]([O:15][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=2)[C:11]([F:12])([F:13])[F:14])[N:22]=[C:17]([NH2:16])[N:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 3472044-Methyl-alpha-(trifluoromethyl)benzenemethanol

Produkt 1

HCID 866142944-Chloro-2-amino-6-[1-(4-methylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 1-(4-methylphenyl)-2,2,2-trifluoro-ethanol (190 mg, 1 mmol) in 10 ml of anhydrous THF. The mixture was stirred for 20 minutes, 2-amino-4,6-dichloro-pyrimidine (164 mg, 1 mmol) was added and then the reaction mixture was heated at 70° C. for 1 hour. After cooling, 5 ml water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 209 mg of 4-chloro-6-[1-(4-methylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamine, yield 66%.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionto extract the product
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe solvent was removed by rotovap

Quellen und Nachweise

ORD-Eintrag
ord-91d2d425198c468697c9c5920d74b94b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093291B2

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