Ammonium Hydroxide → 5-Bromo-7-isopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1910030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910030
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:3]=1.[OH-].[NH4+:18]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:18])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:3]=1

Komponenten

3

Edukt 2

HCID 14923Ammonium HydroxideHCID 866636835-bromo-4-chloro-7-(3-methylbutyl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 668237945-Bromo-7-isopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineAusbeute 97,3 %

Versuchsvorschrift

To 5-bromo-4-chloro-7-(3-methylbutyl)-7H-pyrrolo[2,3-d]pyrimidine (210 mg, 0.694 mmol) in a 5 mL sealable vial was added ammonium hydroxide (1.5 mL, 38.5 mmol). The mixture was then capped and heated at room temp overnight. The reaction was cooled and a precipitate formed. The solid was isolated by filtration and air dried to isolated 5-bromo-7-(3-methylbutyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (191 mg, 0.675 mmol, 97% yield) as a light brown solid. For 50-A1: LC/MS (ES) m/z=283.2, 285.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) 8.10 (s, 1H), 7.48 (s, 1H), 6.70 (br. s., 2H), 4.12 (t, J=7.20 Hz, 2H), 1.64 (q, J=6.99 Hz, 2H), 1.44 (ddd, J=6.69, 6.82, 13.26 Hz, 1H), 0.90 (d, J=6.57 Hz, 6H).

Aufarbeitung

  1. customThe mixture was then capped
  2. temperatureThe reaction was cooled
  3. customa precipitate formed
  4. customThe solid was isolated by filtration and air
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-81294315eec94bdc84531cc5e830046e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

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