Sodium hydride → HCID 178462379, Verbindung

HRID 415362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415362
[H-].[Na+].[BH4-].[Na+].O.[NH2:6][C:7]1[N:12]=[C:11]([SH:13])[N:10]=[C:9]([OH:14])[CH:8]=1.Cl[C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24])[CH3:17]>CN(C=O)C>[NH2:6][C:7]1[N:12]=[C:11]([S:13][C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH3:17])[N:10]=[C:9]([OH:14])[CH:8]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 524203081-[(1R)-1-chloroethyl]-2-fluorobenzeneHCID 178507962HCID 178507962, Verbindung

Produkt 1

HCID 178462379HCID 178462379, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

NaH (60% in oil, 1.05 g, 26.3 mmol) was added in portions followed by NaBH4 (0.099 g, 2.7 mmol) to 6-amino-2-mercaptopyrimidin-4-ol monohydrate (4.23 g, 26.3 mmol) in DMF (40 mL). After 30 minutes, 1-[(1R)-1-chloroethyl]-2-fluorobenzene (5.0 g, 31.5 mmol) in DMF (10 mL) was added and the reaction mixture was stirred for 24 h. The reaction mixture was concentrated and partitioned between water and DCM, the organic phase was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (a stepwise gradient of 5-10% MeOH in CHCl3) to give the title compound (5.20 g, 75% yield).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between water and DCM
  3. dry with materialthe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash column chromatography (a stepwise gradient of 5-10% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-24f4336e22864c95b1294f4bc52a3595
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088780B2

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