N-bromobutanimide → 3-(7-Bromo-5-oxo-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-3-yl)propanoic acid

HRID 1664555Notes

Reaction equation

[O:1]=[C:2]1[N:10]2[C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[N:12][N:13]=[C:9]2[N:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:7]2[N:6]=[CH:5][NH:4][C:3]1=2.C1C(=O)N([Br:31])C(=O)C1>C1COCC1>[Br:31][C:5]1[NH:4][C:3]2[C:2](=[O:1])[N:10]3[C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[N:12][N:13]=[C:9]3[N:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:7]=2[N:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The mixture of 3-(5-oxo-9-pentyl-6,9-dihydro-5H[1,2,4]triazolo[4,3-a]purin-3-yl)propanoic acid (203 mg, 0.64 mmole) and NBS (125.8 mg, 7.0 mmol) in THF (25 ml) was stirred at 70° C. for 2 hours. After evaporation of solvent, the residue was purified by preparative LC-MS to afford 60.2 mg (23.7%) of the desired product (60.2 mg, 23.7%) as white solid. LCMS calculated for C14H18BrN6O3 (M+H): 397.1. found: 371.1.

Workup

customAfter evaporation of solvent
customthe residue was purified by preparative LC-MS

Sources & evidence

ORD record: ord-4d208e5f0a63470984175027602ef0d6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039478B2

Reaction notes

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