Hydrochloric Acid → 7-Benzyl-8-(3-methyloxycarbonyl-cyclopentyl)-1,3-dipropylpurine-2,6-dione

HRID 1684523Notes

Reaction equation

HRID 1684523 reaction equation
Cl.F[C:3](F)(F)[C:4]([OH:6])=[O:5].[CH2:9]([N:16]1[C:24]2[C:23](=[O:25])[N:22]([CH2:26][CH2:27][CH3:28])[C:21](=[O:29])[N:20]([CH2:30][CH2:31][CH3:32])[C:19]=2[N:18]=[C:17]1[CH:33]1[CH2:37]C[C:35](=C2SCCCS2)[CH2:34]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:44]O>ClCCl.[Hg](Cl)Cl>[CH2:9]([N:16]1[C:24]2[C:23](=[O:25])[N:22]([CH2:26][CH2:27][CH3:28])[C:21](=[O:29])[N:20]([CH2:30][CH2:31][CH3:32])[C:19]=2[N:18]=[C:17]1[CH:33]1[CH2:34][CH2:35][CH:3]([C:4]([O:6][CH3:44])=[O:5])[CH2:37]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6422Trifluoroacetic acidHCID 190398217-Benzyl-8-(3-(1,3-dithian-2-ylidene)-cyclopentyl)-1,3-dipropylpurine-2,6-dione

Product 1

HCID 190398367-Benzyl-8-(3-methyloxycarbonyl-cyclopentyl)-1,3-dipropylpurine-2,6-dione

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.2 ml of 6N hydrochloric acid, 0.55 ml of trifluoroacetic acid and 2.38 g (8.8 mmol) of mercury(II)-chloride are successively added to a solution of 1.1 g (2.2 mol) of 7-benzyl-8-(3-(1,3-dithian-2-ylidene)-cyclopentyl)-1,3-dipropylpurine-2,6-dione in 30 ml of methanol and 6 ml of dichloromethane. The mixture is stirred for 4 hours at ambient temperature and then suction filtered over Celite. At -5° C., 90 mg of sodium borohydride are carefully added the filtrate, which is stirred for 30 minutes at 0° C., suction filtered over Celite and evaporated down. For purification the residue remaining is chromatographed on silica gel with a mixture of dichloromethane/methanol in the ratio 97:3. 0.72 g (72% of theory) of the title compound are obtained as a brownish oil.

Workup

  1. filtrationsuction filtered over Celite
  2. additionAt -5° C., 90 mg of sodium borohydride are carefully added the filtrate, which
  3. stirringis stirred for 30 minutes at 0° C.
  4. filtrationsuction filtered over Celite
  5. customevaporated down
  6. customFor purification the residue
  7. customremaining is chromatographed on silica gel with a mixture of dichloromethane/methanol in the ratio 97:3

Sources & evidence

ORD record
ord-b5a499bef1214d88b2827aae6d340f10
Source dataset
uspto-grants-1997_06
Patent number
US05641784

Reaction notes

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