Anisole → HCID 135581776, compound

HRID 1773335Notes

Reaction equation

HRID 1773335 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].COC1C=CC(C[N:12]2[C:17]3=[N:18][N:19]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=5)=[CH:31][CH:30]=4)[C:20]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]3[C:15](=[O:41])[N:14]([CH3:42])[C:13]2=[O:43])=CC=1.C1(OC)C=CC=CC=1>ClCCCl>[CH3:42][N:14]1[C:15](=[O:41])[C:16]2=[C:20]([NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:19]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:33][CH:34]=3)[N:18]=[C:17]2[NH:12][C:13]1=[O:43]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 24781793HCID 24781793, compound

Product 1

HCID 135581776HCID 135581776, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

AlCl3 (0.733 g, 5.50 mmol) is added to a solution of 7-(4-methoxybenzyl)-5-methyl-3-(phenylamino)-2-(4-(pyridin-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (1.08 g, 1.98 mmol) and anisole (mL) in 1,2-dichloroethane (15 mL) under argon. The reaction mixture is stirred at room temperature overnight, and then quenched with water with cooling. The resulting suspension is treated with 20% NaOH (70 mL), and then extract with methylene chloride 5 times. The organic phase is combined and evaporated to dryness. The residue is further purified by chromatography to give 751 mg of pure product (Yield: 89%). MS (FAB) m/z 425.3 [M+H]+.

Workup

  1. customquenched with water
  2. temperaturewith cooling
  3. additionThe resulting suspension is treated with 20% NaOH (70 mL)
  4. extractionextract with methylene chloride 5 times
  5. customevaporated to dryness
  6. customThe residue is further purified by chromatography

Sources & evidence

ORD record
ord-7374d5f355cb4482a8c1e2cc3ec25855
Source dataset
uspto-grants-2016_02
Patent number
US09255099B2

Reaction notes

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