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

HRID 2389530ノート

反応式

HRID 2389530 の反応式
[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

参加物

6

反応物 3

HCID 180504Ceric ammonium nitrate2 回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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-7e0157dbfc304ea681015cb36a6d728d
出典データセット
uspto-grants-2012_09
特許番号
US08273750B2

反応ノート

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