Potassium Carbonate → (R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-butyramide

HRID 1041733

Reaktionsgleichung

Reaktionsgleichung von HRID 1041733
[NH2:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4].[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([Cl:17])=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[Cl:9][C:10]1[N:15]=[C:14]([NH:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4])[C:13]([Cl:17])=[CH:12][N:11]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 444079(R)-2-amino-3-methylbutanamide

Produkt 1

HCID 86634077(R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-butyramideAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (R)-2-amino-3-methyl-butyramide (50 mg), 2,4,5-trichloropyrimidine (67 mg) and K2CO3 (116 mg) in DMF (3 mL) was stirred at room temperature for 5 hr. The reaction mixture was diluted with DCM and washed with brine three times. The organic layer was dried with sodium sulfate and concentrated. The residue was purified by silica gel chromatography to provide 60 mg of (R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-butyramide: 1H NMR (300 MHz, CDCl3) 8.2 (s, 1H), 6.2 (bs, 1H), 5.8 (bs, 1H), 5.6 (bs, 1H), 4.6 (dd, 1H), 2.4 (m, 1H), 1.2 (d, 6H). MS (m/e) 263 (M+1).

Aufarbeitung

  1. washwashed with brine three times
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ca9b4177ec1d419692fd65d148724ee5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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