Trityl chloride → HCID 22007310, compound

HRID 323875Notes

Reaction equation

HRID 323875 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][NH:9][C:8]=2[C:7](=[O:13])[NH:6][C:5]1=[O:14].[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][N:9]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:8]=2[C:7](=[O:13])[NH:6][C:5]1=[O:14]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 706393-Methylxanthine

Product 1

HCID 22007310HCID 22007310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

0.62 g (25.88 mmol) of sodium hydride was added in portions at 60° C. to a suspension of 3.9 g (23.5 mmol) of 3-methylxanthine in 85 ml of dimethylformamide, and the mixture was stirred at this temperature for 1.5 hours and heated to 90° C. 6.6 g (23.67 mmol) of trityl chloride in 30 ml of dimethylformamide were then added and the mixture was stirred at 90° C. for 3 hours. The solid was then filtered off hot with suction and the filtrate was concentrated under reduced pressure, the residue was taken up in 1 N sodium hydroxide solution, the mixture was heated to 80° C. and the solid was filtered off with suction. The filtrate was brought to pH 4-5 using 2 N hydrochloric acid. The precipitate formed in this way was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19/0.2). Yield:

Workup

  1. stirringthe mixture was stirred at 90° C. for 3 hours
  2. filtrationThe solid was then filtered off hot with suction
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. temperaturethe mixture was heated to 80° C.
  5. filtrationthe solid was filtered off with suction
  6. customThe precipitate formed in this way
  7. customwas purified by flash chromatography on a silica gel column, dichloromethane/methanol (19/0.2)

Sources & evidence

ORD record
ord-3e9f0cc5406940839e7015dc207494bf
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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