[4-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)phenyl]methanol → 4-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)benzaldehyde

HRID 1666204Notes

Reaction equation

HRID 1666204 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:33][CH3:34])[N:6]2[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:33][CH3:34])[N:6]2[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([CH:31]=[O:32])=[CH:29][CH:30]=2)[CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 59288029[4-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)phenyl]methanol

Product 1

HCID 592880284-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)benzaldehydeYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

The compound (0.52 g, 1.10 mmol) obtained in Step (i) and manganese dioxide (0.95 g, 11.0 mmol) were added to chloroform (20 ml), and the mixture was stirred at room temperature for 15 hours. The mixture was filtered, and the filtrate was concentrated. The residue was purified by silica gel column (chloroform/methanol=100/1 to 50/1) to give the subtitle compound (0.47 g, 1.00 mmol) as a white solid. Yield: 92%.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column (chloroform/methanol=100/1 to 50/1)

Sources & evidence

ORD record
ord-a92d55ffa30b49ef815a629de1aacc34
Source dataset
uspto-grants-2011_10
Patent number
US08044056B2

Reaction notes

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