Methanol → 7-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-ol

HRID 860089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860089
[NH:1]1[C:5]2=[N:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:24])[CH:15]=[CH:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[N:21][CH:22]=3)=[CH:8][CH:9]=[C:4]2[CH2:3][CH2:2]1.CO.[BH4-].[Na+]>C1COCC1>[NH:1]1[C:5]2=[N:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:24])[CH:15]=[CH:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[N:21][CH:22]=3)=[CH:8][CH:9]=[C:4]2[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 696668007-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-one

Produkt 1

HCID 696663717-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-olAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the enone 23-8 (0.400 g, 1.24 mmol) in THF:MeOH (5 mL each) was treated with NaBH4 (0.047 g, 1.24 mmol). The reaction was quenched with acetone (2 mL), concentrated in vacuo, partitioned between water (5 mL) and chloroform (5 mL), and extracted with chloroform (4×10 mL). The organics were combined, dried (Na2SO4), and concentrated in vacuo to afford 0.387 g (96% yield) of 23-9.

Aufarbeitung

  1. customThe reaction was quenched with acetone (2 mL)
  2. concentrationconcentrated in vacuo
  3. custompartitioned between water (5 mL) and chloroform (5 mL)
  4. extractionextracted with chloroform (4×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6649ab28eac442528293c7ea3c90b8d1
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153862B2

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