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Ethyl Acetate → 2-Methylsulfanyl-6-(3-trifluoromethylphenyl)-pyrimidin-4-ylamine

HRID 2053084
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2053084
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][S:9][C:4]1[N:3]=[C:2]([NH2:1])[CH:7]=[C:6]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:12]([F:23])([F:22])[F:11])[CH:18]=2)[N:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 704964-Amino-6-chloro-2-methylthiopyrimidineHCID 27343883-(Trifluoromethyl)phenylboronic acid

Produkt 1

HCID 585132282-Methylsulfanyl-6-(3-trifluoromethylphenyl)-pyrimidin-4-ylamineAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-amino-6-chloro-2-methylthiopyrimidine (3.5 g) in toluene (45 mL) under a nitrogen atmosphere was added, sequentially, 3-(trifluoromethyl)phenylboronic acid (4.15 g), potassium carbonate (25 mL, 2M) and tetrakis(triphenylphosphine)palladium(0) (1.16 g). The mixture was heated to reflux for ten hours. Ethyl acetate (150 mL) was added and the mixture washed with water (2×100 mL). Organic layer was separated, washed with saturated sodium chloride (100 mL), dried over sodium sulphate and solvent was evaporated under reduced pressure to yield crude product. Purification by flash chromatography yielded product 2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ylamine (3.45 g)

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for ten hours
  3. washthe mixture washed with water (2×100 mL)
  4. customOrganic layer was separated
  5. washwashed with saturated sodium chloride (100 mL)
  6. dry with materialdried over sodium sulphate and solvent
  7. customwas evaporated under reduced pressure
  8. customto yield crude product
  9. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a34b067471a64c818b8713335d50002e
Quelldatensatz
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07326715B2

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