Triethylamine → (R)-2-(2-chloro-5-iodopyrimidine-4-ylamino)propan-1-ol

HRID 238144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238144
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([I:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:17][C@H:18]([CH3:21])[CH2:19][OH:20]>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C@H:18]([CH3:21])[CH2:19][OH:20])[C:5]([I:9])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 2634382,4-Dichloro-5-iodopyrimidine

Produkt 1

HCID 59550865(R)-2-(2-chloro-5-iodopyrimidine-4-ylamino)propan-1-olAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2,4-dichloro-5-iodopyrimidine (3.0 g; 10.9 mol) in acetonitrile (35 mL) was added triethylamine (1.32 g, 1.82 mL, 13.1 mmol), followed by (R)-2-aminopropanol (0.88 g, 11.8 mmol). The mixture was stirred at room temperature for 24 h and was then diluted with ethyl acetate, followed by extraction with brine, 10% aqueous citric acid, and aqueous sodium bicarbonate. After drying over sodium sulfate, the solvent was evaporated and the residue was purified by column chromatography to give the title compound (3.0 g, 88% yield).

Aufarbeitung

  1. extractionfollowed by extraction with brine, 10% aqueous citric acid, and aqueous sodium bicarbonate
  2. dry with materialAfter drying over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cd889b014b5549db88072404b9fce243
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642611B2

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