Ammonium Hydroxide → 5-bromo-7-(3-oxetanyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1910064Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:12]2[CH2:15][O:14][CH2:13]2)[CH:3]=1.[OH-].[NH4+:17]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:17])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:12]2[CH2:15][O:14][CH2:13]2)[CH:3]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 866636865-bromo-4-chloro-7-(3-oxetanyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 668240635-bromo-7-(3-oxetanyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 61.5%

Conditions

Temperature: 85 °C

Procedure

To 5-bromo-4-chloro-7-(3-oxetanyl)-7H-pyrrolo[2,3-d]pyrimidine (185 mg, 0.641 mmol) was added ammonium hydroxide (24.97 μl, 0.641 mmol) in a 25 ml sealable vial and heated at 85° C. over 24 hr. The solid was isolated by filtration and washed with water (5 mL) and dried to give 5-bromo-7-(3-oxetanyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (106 mg), which was used without further purification.

Workup

customThe solid was isolated by filtration
washwashed with water (5 mL)
customdried

Sources & evidence

ORD record: ord-51cfc3000dbb4fd08298e36cd8c7a6eb
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598156B2

Reaction notes

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