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

Reaction equation

[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH3:12])[CH:3]=1.[OH-].[NH4+:14]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:14])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH3:12])[CH:3]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 665451605-Bromo-4-chloro-7-methyl-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 665609385-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 79.8%

Conditions

Temperature: 100 °C

Procedure

A suspension of 5-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (17 g, 69.0 mmol) in ammonium hydroxide (150 mL, 3852 mmol) was stirred for 2 days at 100° C. in a sealed vessel. The reaction was allowed to cool to room temperature and filtered. The collected solid was washed with Et2O to afford the product 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (12.5 g) as a white solid.

Workup

temperatureto cool to room temperature
filtrationfiltered
washThe collected solid was washed with Et2O

Sources & evidence

ORD record: ord-0d37edfcb1604732885826ec3915d32b
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598156B2

Reaction notes

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