Tert-Butylamine → 4'-Phenyl-2-(tert-butylamino)acetophenone hydrobromide

HRID 611518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611518
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18]>C(#N)C>[BrH:1].[C:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][NH:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 6385Tert-ButylamineHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanone

Produkt 1

HCID 195974384'-Phenyl-2-(tert-butylamino)acetophenone hydrobromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

This Example was carried out in a similar manner to Example 2. 2-Bromo-4'-phenylacetophenone (25.0 g) in acetonitrile (150 ml) was reacted with tert-butylamine (28.4 ml) to give 4'-phenyl-2-(tert-butylamino)acetophenone hydrobromide (5.31 g) m.p. 234-237° C. (with decomposition). This compound was reacted with malononitrile (1.7 g) and potassium hydroxide (3.0 g) in water (4 ml) in methanol (100 ml) under nitrogen to give 2-amino-4-(4-biphenylyl)-3-cyano-1-(tert-butyl)pyrrole (3.75 g) which was suspended in formamide (200 ml) saturated with ammonia and then the mixture was heated at 200-205° C. for two hours whilst ammonia was being passed through the mixture. After cooling the mixture was added to ice-water (600 g) under nitrogen and the solid collected by filtration, purified by flash column chromatography on silica using ethyl acetate/triethylamine (19:1) as the mobile phase to give 5-(4-biphenylyl)-7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 212-214° C.

Quellen und Nachweise

ORD-Eintrag
ord-3e0b6ad1474b4a879e108187498587d7
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001839

Notizen zur Reaktion

Wird geladen…