Ammonium Hydroxide → 5-Bromothieno[2,3-D]pyrimidin-4-amine

HRID 1909955

Reaction equation

[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[OH-].[NH4+:13]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:13])=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 454802995-Bromo-4-chlorothieno[2,3-d]pyrimidine

Product 1

HCID 668238985-Bromothieno[2,3-D]pyrimidin-4-amineYield 86.3%

Conditions

Temperature: 90 °C

Procedure

A suspension of 5-bromo-4-chlorothieno[2,3-d]pyrimidine (1 g, 4.01 mmol) in concentrated aqueous ammonium hydroxide (150 mL, 3852 mmol) was stirred overnight at 90° C. in a sealed vessel. The reaction was allowed to cool to room temperature and filtered. The white solid in the filter was air dried to afford 5-bromothieno[2,3-d]pyrimidin-4-amine (796 mg). LC/MS (ES) m/z=387.1 [M+H]+.

Workup

temperatureto cool to room temperature
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-443a428a30dd4020bd5d2bdeacc9c33a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598156B2

Linked notes

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