Ceric ammonium nitrate → 3-Benzyl-2-(biphenyl-4-ylmethyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 2389530

Reaction equation

HRID 2389530 reaction equation
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[CH2:23]([C:30]1[N:31]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:54][CH:53]=2)[N:32]=[C:33]2[C:38]=1[C:37](=[O:39])[N:36]([CH3:40])[C:35](=[O:41])[N:34]2CC1C=CC(OC)=CC=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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+]>O.C1COCC1>[CH2:23]([C:30]1[N:31]([CH2:51][C:52]2[CH:53]=[CH:54][C:55]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:56][CH:57]=2)[N:32]=[C:33]2[C:38]=1[C:37](=[O:39])[N:36]([CH3:40])[C:35](=[O:41])[NH:34]2)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 180504Ceric ammonium nitrate2×HCID 9869224Ammonium cerium (IV) nitrateHCID 667956863-benzyl-2-(biphenyl-4-ylmethyl)-7-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 1363512593-Benzyl-2-(biphenyl-4-ylmethyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ammonium cerium (IV) nitrate (204 mg, 0.371 mmol) in water (0.6 mL) is added to a solution of 3-benzyl-2-(biphenyl-4-ylmethyl)-7-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (40.3 mg, 0.0743 mmol) in THF (2 mL). The resulting orange solution is stirred at room temperature overnight. Another batch of CAN (204 mg, 0.371 mmol) is added and the mixture is stirred for 3 hours, and then the third batch of CAN (204 mg) is added, and the mixture is stirred at r.t. overnight. The reaction mixture is evaporated to dryness. The residue is treated with brine, and extracted with methylene chloride five times. The organic phase is combined and concentrated. The residue is purified by chromatography to give 11.6 mg product as white solids (Yield: 36.9%). 1H NMR (400 MHz, acetone-d6) δ 3.27 (s, 3H), 4.51 (s, 2H), 5.33 (s, 2H), 7.13-7.62 (m, 14H), 10.26 (s, 1H). MS (FAB) m/z 423.2 [M+H]+.

Workup

  1. stirringthe mixture is stirred for 3 hours
  2. stirringthe mixture is stirred at r.t. overnight
  3. customThe reaction mixture is evaporated to dryness
  4. additionThe residue is treated with brine
  5. extractionextracted with methylene chloride five times
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-7e0157dbfc304ea681015cb36a6d728d
Source dataset
uspto-grants-2012_09
Patent number
US08273750B2

Linked notes

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