1,1'-Carbonyldiimidazole → 4-Pentyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

HRID 2374331Notes

Reaction equation

[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]1[NH:16][N:15]=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1N=CN([C:22](N2C=NC=C2)=[O:23])C=1>O1CCOCC1>[CH2:1]([N:6]1[C:7]2[N:8]=[CH:9][NH:10][C:11]=2[C:12]2=[N:13][CH:14]=[N:15][N:16]2[C:22]1=[O:23])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-pentyl-5-(1H-1,2,4-triazol-5-yl)-1H-imidazol-4-amine (0.52 g, 2.4 mmol) and N,N-carbonyldiimidazole (0.57 g, 3.5 mmol) in 1,4-dioxane (10 mL) was stirred at 110° C. for 2 hours. The solvent was removed under reduced pressure, and the residue was purified by preparative LCMS to yield the desire product (30 mg, 5% yield). LCMS calculated for C11H15N6O (M+H): 247.1; found: 247.1.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by preparative LCMS

Sources & evidence

ORD record: ord-c33e6e209cdb47968b5fc387a513dd28
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462624B2

Reaction notes

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