5-Aminovaleric acid → 5-((7-(3-aminopropyl)-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pentanoic acid

HRID 920678Notes

Reaction equation

[Br:1][C:2]1[C:10]2[CH:9]=[N:8][C:7](Cl)=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH:3]=1.[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32]>C1COCC1.O>[NH2:15][CH2:14][CH2:13][CH2:12][N:4]1[C:5]2[N:6]=[C:7]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:8]=[CH:9][C:10]=2[C:2]([Br:1])=[CH:3]1

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of the crude 2-(3-(5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propyl)isoindoline-1,3-dione in a mixture of THF and water (10 mL, 3:2, v/v) was added 5-aminopentanoic acid (172.3 mg, 1.47 mmol). The resulting mixture was heated at 150° C. under microwave irradiation for 1 h. After the solvent was removed, the residue was dissolved in a mixture of ethanol and water (20 mL, 3:2, v/v) followed by the addition of hydrazine (1.5 mL). Then the reaction mixture was heat at 80° C. for overnight. The solvent was removed and the residue was purified on HPLC to provide 5-((7-(3-aminopropyl)-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pentanoic acid as an clear oil (MS m/z 371.10 [M+H]+).

Workup

customAfter the solvent was removed
dissolutionthe residue was dissolved in a mixture of ethanol and water (20 mL, 3:2
additionv/v) followed by the addition of hydrazine (1.5 mL)
temperatureThen the reaction mixture was heat at 80° C. for overnight
customThe solvent was removed
customthe residue was purified on HPLC

Sources & evidence

ORD record: ord-c7d362939777417a972ec72a150deebf
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273056B2

Reaction notes

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