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Nitric Acid → HCID 58212080, compound

HRID 1616104
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 30699711H-Imidazo(2,1-f)purine-2,4(3H,8H)-dione, 8-butyl-1-methyl-7-phenyl-

Product 1

HCID 58212080HCID 58212080, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 887
Methanol
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765775B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes