Acetonitrile → (R)-3-(5-acetoxyhexyl)-1-methyl-6,7,8,9-tetrahydro-pyrimido[2, 1-f]purine-2,4(1H,3H)-dione

HRID 1296415Notes

Reaction equation

HRID 1296415 reaction equation
[C:1]([O:4][C@H:5]([CH3:33])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][CH2:22]NC(OC(C)(C)C)=O)[C:16](Br)=[N:15][C:14]=2[N:13]([CH3:32])[C:11]1=[O:12])(=[O:3])[CH3:2].FC(F)(F)C(O)=O.ClCCl.C(=O)([O-])[O-].[K+].[K+].[C:50](#[N:52])C>>[C:1]([O:4][C@H:5]([CH3:33])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]3[CH2:21][CH2:22][CH2:50][NH:52][C:16]3=[N:15][C:14]=2[N:13]([CH3:32])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 69154900(R)-1-(5-acetoxyhexyl)-8-bromo-7-(2-(N-tert-butoxycarbonylamino)ethyl)-3-methylxanthine

Product 1

HCID 136368770(R)-3-(5-acetoxyhexyl)-1-methyl-6,7,8,9-tetrahydro-pyrimido[2, 1-f]purine-2,4(1H,3H)-dioneYield 88%

Procedure

(R)-1-(5-acetoxyhexyl)-8-bromo-7-(2-(N-tert-butoxycarbonylamino)ethyl)-3-methylxanthine (6.10 g, 11.2 mmol) was added to a solution of trifluoroacetic acid (50 ml) and dichloromethane (50 ml) and stirred at room temperature for 3 hours. Concentration under reduced pressure provided an oil to which was added acetonitrile (30 ml) followed by potassium carbonate (13.8 g, 100 mmol). The mixture was stirred at 650° C. for 3 hours and filtered to remove solids. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with ethyl acetate-methanol (4:1) to provide (R)-3-(5-acetoxyhexyl)-1-methyl-6,7,8,9-tetrahydro-pyrimido[2,1-f]purine-2,4(1H,3H)-dione (3.58 g, 88% yield) as a white powder.

Workup

  1. concentrationConcentration under reduced pressure
  2. customprovided an oil to which
  3. stirringThe mixture was stirred at 650° C. for 3 hours
  4. filtrationfiltered
  5. customto remove solids
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate-methanol (4:1)

Sources & evidence

ORD record
ord-d8c5897b8f7847209da1427db9e3e6d0
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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