Nitric Acid → HCID 58212080, compound

HRID 1616104Notes

Reaction equation

HRID 1616104 reaction equation
[CH2:1]([N:5]1[C:9]2=[N:10][C:11]3[N:12]([CH3:19])[C:13](=[O:18])[NH:14][C:15](=[O:17])[C:16]=3[N:8]2[CH:7]=[C:6]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH3:4].[N+:26]([O-])([OH:28])=[O:27].O>C(O)(=O)C.CO>[CH2:1]([N:5]1[C:9]2=[N:10][C:11]3[N:12]([CH3:19])[C:13](=[O:18])[NH:14][C:15](=[O:17])[C:16]=3[N:8]2[C:7]([N+:26]([O-:28])=[O:27])=[C:6]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 30699718-Butyl-4-hydroxy-1-methyl-7-phenyl-1H-imidazo[2,1-f]purin-2(8H)-one

Product 1

HCID 58212080HCID 58212080, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of commercially available 8-butyl-1-methyl-7-phenyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione (3, 100 mg, 0.296 mmol) in acetic acid (500 μL) was added HNO3 (fuming, 24 μL, 0.592 mmol), and the resulting mixture was stirred at room temperature for 12 h. Water was added, and the resulting precipitate was filtered off. Cristallization in methanol afforded the desired product as a yellow solid (26 mg, 23% yield). 1H NMR (400 MHz, DMSO-d6): δ=11.05 (s, 1H), 7.60-7.69 (m, 5H), 3.93 (t, J=7.3 Hz, 2H), 3.43 (s, 3H), 1.62 (quint, J=7.3 Hz, 2H), 1.14 (sext, J=7.3 Hz, 2H), 0.70 (t, J=7.3 Hz, 3H); 13C NMR (100 MHz, DMSO-d6): δ=153.4, 152.1, 150.5, 144.6, 134.4, 130.9, 130.7, 128.5, 126.9, 124.7, 101.6, 44.3, 29.5, 29.0, 18.6, 12.9; IR (film) ν=3172, 3052, 2964, 1693, 1502, 1356, 1294, 732, 577 cm−1; HRMS (ESI): m/z: calcd for C18H18N6O4Na+: 405.1287, found: 405.1288.

Workup

  1. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-7dcaa24b3f594f559042f3f58b25adb5
Source dataset
uspto-grants-2014_07
Patent number
US08765775B2

Reaction notes

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