N-bromobutanimide → 8-Bromo-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one

HRID 249772Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

The mixture of 6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one (0.020 g, 0.081 mmol) and N-bromosuccinimide (10 mg, 8.0 mmol) in acetonitrile (2 mL) in a 5 mL-microwave reaction tube was heated at 70° C. in microwave oven for 12 min. After cooling down to room temperature, the reaction mixture was purified using preparative LCMS to yield the desired product as a white powder. LCMS calculated for C10H13BrN7O (M+H): 326.0, 328.0. found: 326.0, 328.0.

Workup

customin a 5 mL-microwave reaction tube
temperatureAfter cooling down to room temperature
customthe reaction mixture was purified

Sources & evidence

ORD record: ord-1799a708fa4f4835aae63c117e83de25
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863285B2

Reaction notes

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