(R)-(-)-2-Amino-1-propanol → 2-[[(2,3-Difluorophenyl)methyl]thio]4-[[(1R)-2-hydroxy-1-methylethyl]amino]-7(8H)-pteridinone

HRID 2105141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105141
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:20]=[C:19](SCC2C=CC=C(F)C=2F)[C:18]2[N:17]=[CH:16][C:15](=[O:31])[NH:14][C:13]=2[N:12]=1.[NH2:32][C@@H:33]([CH2:35][OH:36])[CH3:34]>>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:20]=[C:19]([NH:32][C@H:33]([CH3:34])[CH2:35][OH:36])[C:18]2[N:17]=[CH:16][C:15](=[O:31])[NH:14][C:13]=2[N:12]=1

Komponenten

3

Edukt 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 225060122,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7(8h)-pteridinone

Produkt 1

HCID 444550142-[[(2,3-Difluorophenyl)methyl]thio]4-[[(1R)-2-hydroxy-1-methylethyl]amino]-7(8H)-pteridinoneAusbeute 11,7 %

Versuchsvorschrift

The product of example 2, step (g) (2.3 g) and D-alaninol (5 g) were microwaved at 150° C. for 5 min. The resulting solution was partitioned between ethyl acetate and aqueous ammonium chloride and the organic layer was washed with ammonium chloride (2×50 ml). The organic layer was evaporated to dryness and purified twice by silica gel chromatography using first 20:1 DCM:methanol and then 1:1 DCM:ethyl acetate to yield the titled compound (220 mg).

Aufarbeitung

  1. customThe resulting solution was partitioned between ethyl acetate and aqueous ammonium chloride
  2. washthe organic layer was washed with ammonium chloride (2×50 ml)
  3. customThe organic layer was evaporated to dryness
  4. custompurified twice by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-445c123b964e422fb0922d519ea347fc
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579342B2

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