Formaldehyde → HCID 20773488, compound

HRID 1814969Notes

Reaction equation

HRID 1814969 reaction equation
N[C@H:2]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[NH:14][C:13]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:12][C:11]=2[N:10]([CH3:27])[C:8]1=[O:9].[CH2:29]=O.[C:31]([BH3-])#[N:32].[Na+]>CO>[CH3:29][N:32]([CH3:31])[C@H:2]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[NH:14][C:13]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:12][C:11]=2[N:10]([CH3:27])[C:8]1=[O:9]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20773485HCID 20773485, compound

Product 1

HCID 20773488HCID 20773488, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-1-(5-aminohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.4 g, 1.0 mmol) in methanol (10 ml) was added formaldehyde (37% in water) (0.4 ml) followed by sodium cyanoborohydride (0.1 g, 1.5 mmol). After stirring at room temperature for 1 hour, the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with ammonium hydroxide (37% in water)-methanol-ethyl acetate mixture (1:5:10) to give (R)-1-(5-dimethylaminohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.20 g, 47% yield) as an oil.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe crude product was purified by flash chromatography on silica gel eluting with ammonium hydroxide (37% in water)-methanol-ethyl acetate mixture (1:5:10)

Sources & evidence

ORD record
ord-7a827dce5e244aea85abafde1dcb7c48
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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