Acetic Anhydride → (R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine

HRID 1355388Notes

Reaction equation

HRID 1355388 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]1[NH:13][C:12]2[C:11](=[O:14])[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:9](=[O:22])[N:8]([CH3:23])[C:7]=2[N:6]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:31]([O:21][C@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][N:10]1[C:11](=[O:14])[C:12]2[NH:13][C:5]([NH:4][CH2:3][CH2:2][Cl:1])=[N:6][C:7]=2[N:8]([CH3:23])[C:9]1=[O:22])(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69154242(R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine

Product 1

HCID 69154552(R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthineYield 89.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a stirring mixture of (R)-8-(2-chloroethylamino)-1-(5-hydroxyhexyl)-3-methylxanthine (2.2 g, 6.4 mmol), triethylamine (1.94 g, 19.2 mmol) and 4-dimethylaminopyridine (0.39 g, 3.2 mmol) in chloroform (50 ml) at 0-5° C. was added acetic anhydride (1.30 g, 12.8 mmol). The mixture was warmed to room temperature, stirred overnight, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethylacetate-methanol (7:1) to provide (R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine (2.2 g, 89% yield) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography
  3. washeluting with ethylacetate-methanol (7:1)

Sources & evidence

ORD record
ord-83cfed07d84b4bb686c1d2280c026b61
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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