Sodium borohydride → 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-hydroxymethyl-2-methylpyrimidine

HRID 1271132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271132
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]([C:12]1[C:17]([CH:18]=[O:19])=[C:16]([NH:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[N:15]=[C:14]([CH3:26])[N:13]=1)[CH2:6][CH2:5]2.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]([C:12]1[C:17]([CH2:18][OH:19])=[C:16]([NH:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[N:15]=[C:14]([CH3:26])[N:13]=1)[CH2:6][CH2:5]2

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 10178654HCID 10178654, Verbindung

Produkt 1

HCID 101575044-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-hydroxymethyl-2-methylpyrimidineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-formyl-2-methylpyrimidine, (50 mg, 0.13 mmol) was stirred with NaBH4 (7 mg, 0.2 mmol) in dry ethanol (2 mL) at 0° C. for 2 h. The reaction was partitioned between EtOAc (100 mL) and water (20 mL) and the EtOAc was washed with brine, dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 40% EtOAc/hexanes to give the product, 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-hydroxymethyl-2-methylpyrimidine (40 mg, 80% yield).

Aufarbeitung

  1. customThe reaction was partitioned between EtOAc (100 mL) and water (20 mL)
  2. washthe EtOAc was washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe residue was chromatographed on silica gel using 40% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9f46dbe143174a4aa765d3594323e1c6
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205306B2

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