N-bromobutanimide → 7-bromo-9-pentyl-3-(3-bromobenzyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 1664547Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][C:6]1[N:10]2[C:11](=[O:23])[C:12]3[NH:13][CH:14]=[N:15][C:16]=3[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:9]2=[N:8][N:7]=1.[Br:27]N1C(=O)CCC1=O>O1CCCC1>[Br:27][C:14]1[NH:13][C:12]2[C:11](=[O:23])[N:10]3[C:6]([CH2:5][C:4]4[CH:24]=[CH:25][CH:26]=[C:2]([Br:1])[CH:3]=4)=[N:7][N:8]=[C:9]3[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:16]=2[N:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To the solution of 3-(3-bromobenzyl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (210 mg, 0.50 mol) in tetrahydrofuran (20 mL) was added N-bromosuccinimide (140 mg, 0.00076 mol). The mixture was stirred at 70° C. for 1 hour. The reaction mixture was concentrated and the residue was purified by preparative LCMS to yield the desired product (0.15 g, 60%). 1HNMR (300 MHz, d6-DMSO): δ 7.16 (d, J=8.3 Hz, 2H), 6.81 (d, J=8.3 Hz, 2H), 4.46 (s, 3H), 4.20 (t, J=7.2 Hz, 2H), 3.67 (s, 2H), 1.79 (m, 2H), 1.28 (m, 4H), 0.83 (m, 3H). LCMS calculated for C18H19Br2N6O (M+H): 493. found: 493, 495 and 497.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by preparative LCMS

Sources & evidence

ORD record: ord-b44e19c0f68b4388bc9b345e64c293d5
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039478B2

Reaction notes

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