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

HRID 1787790Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To the mixture of 9-pentyl-3-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (50 mg, 0.16 mmol) in tetrahydrofuran (10 mL) was added N-bromosuccinimide (42 mg, 0.24 mmol). The mixture was stirred at 70° C. for 3 hour. The reaction mixture was concentrated and purified by preparative LCMS to yield the desired product. 1HNMR (300 MHz, CD3OD): δ 4.44 (t, J=7.6 Hz, 2H), 1.94 (m, 2H), 1.42 (m, 4H), 0.93 (m, 3H). LCMS calculated for C12H13BrF3N6O(M+H): 393.0, found: 393.0, 395.0.

Workup

concentrationThe reaction mixture was concentrated
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-fe69eed9dcbb4952854932a6a57d0406
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511050B2

Reaction notes

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