1,1'-Carbonyldiimidazole → 4-pentyl-8-phenyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

HRID 249775Notes

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]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1COCC1>[CH2:1]([N:6]1[C:7]2[N:8]=[CH:9][NH:10][C:11]=2[C:12]2=[N:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]2[C:28]1=[O:29])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 70 °C

Procedure

N-pentyl-5-(3-phenyl-1H-1,2,4-triazol-5-yl)-1H-imidazol-4-amine (50 mg, 0.17 mmol) and N,N-carbonyldiimidazole (50 mg, 0.3 mmol) were dissolved in THF (10 mL) and stirred at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by preparative LCMS (method B) to yield the desired product (25 mg, 45% yield). LCMS calculated for C17H19N6O(M+H): 323.2. found 323.1.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by preparative LCMS (method B)

Sources & evidence

ORD record: ord-cae17427a9464405938ae0a7d72cb9a8
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863285B2

Reaction notes

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