Ceric ammonium nitrate → N7-((2-Hydroxyethoxy)methyl)guanine

HRID 2417224Notes

Reaction equation

HRID 2417224 reaction equation
COC1C=CC([O:9][CH2:10][CH2:11][O:12][CH2:13][N:14]2[C:22]3[C:21](=[O:23])[NH:20][C:19]([NH2:24])=[N:18][C:17]=3[N:16]=[CH:15]2)=CC=1.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>CC#N.O>[OH:9][CH2:10][CH2:11][O:12][CH2:13][N:14]1[C:22]2[C:21](=[O:23])[NH:20][C:19]([NH2:24])=[N:18][C:17]=2[N:16]=[CH:15]1

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 135407768HCID 135407768, compound

Product 1

HCID 135449026N7-((2-Hydroxyethoxy)methyl)guanineYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 8 (1.36 g, 4.10 mmol) in a mixture of CH3CN (30 mL) and water (10 mL) was added CAN (2.25 g, 4.10 mmol) at 0° C. The stirred reaction mixture was allowed to warm-up to 25° C. within 1.0 h. Water (30 mL) was added to afford a solid. Filtration and crystallization of the solid from EtOH/water (4:1) gave 9 (0.65 g, 2.88 mmol) in 70% yield: mp>280° C. (dec.); Rf(hexanes/EtOAc=1:2) 0.08; UV (EtOH) λmax 289 (ε 16,000); 1H NMR (DMSO-d6) δ 3.61-3.82 (m, 4H, O(CH2)2O), 4.85 (br s, 1H, OH), 5.81 (s, 2 H, H2C1′), 5.96 (br s, 2 H, NH2), 6.61 (s, 1 H, NH), 8.67 (s, 1 H, HC8); 13C NMR (DMSO-d6) δ 60.91 (CH2OH), 70.01 (OCH2) 75.25 (C1′), 107.16 (C5), 143.92 (C8), 153.20 (C4), 154.40 (C2), 159.30 (C6); MS m/z 225 (M+). Anal (C8H11N5O3) C, H, N; calcd (%): 42.66, 4.92, 31.10; found (%): 42.75, 4.84, 31.21.

Workup

  1. customThe stirred reaction mixture
  2. customto afford a solid
  3. filtrationFiltration and crystallization of the solid from EtOH/water (4:1)

Sources & evidence

ORD record
ord-4a4a8624bb74488cabc03354a5840aea
Source dataset
uspto-grants-2004_11
Patent number
US06825348B2

Reaction notes

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