Water → 7-Benzyl-8-(3-(1,3-dithian-2-ylidene)-cyclopentyl)-1,3-dipropylpurine-2,6-dione

HRID 1684522Notes

Reaction equation

HRID 1684522 reaction equation
C([Li])CCC.C[Si](C)(C)[CH:8]1[S:13][CH2:12][CH2:11][CH2:10][S:9]1.[CH2:16]([N:23]1[C:31]2[C:30](=[O:32])[N:29]([CH2:33][CH2:34][CH3:35])[C:28](=[O:36])[N:27]([CH2:37][CH2:38][CH3:39])[C:26]=2[N:25]=[C:24]1[CH:40]1[CH2:44][CH2:43][C:42](=O)[CH2:41]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CCCCCC.O1CCCC1>[CH2:16]([N:23]1[C:31]2[C:30](=[O:32])[N:29]([CH2:33][CH2:34][CH3:35])[C:28](=[O:36])[N:27]([CH2:37][CH2:38][CH3:39])[C:26]=2[N:25]=[C:24]1[CH:40]1[CH2:41][CH2:42][C:43](=[C:8]2[S:13][CH2:12][CH2:11][CH2:10][S:9]2)[CH2:44]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 834132-Trimethylsilyl-1,3-dithianeHCID 149891347-Benzyl-8-(3-oxocyclopentyl)-1,3-dipropylpurine-2,6-dioneHCID 178418339Butyllithium

Product 1

HCID 190398217-Benzyl-8-(3-(1,3-dithian-2-ylidene)-cyclopentyl)-1,3-dipropylpurine-2,6-dione

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

At -75° C. 14.37 ml (0.023 mol) of a 1.6M solution of butyl lithium in n-hexane is added dropwise to 4.0 g of 2-trimethylsilyl-1,3-dithiane (0.021 mol) in 15 ml of absolute tetrahydrofuran and the mixture is stirred for a further 30 minutes at -70° C. Then at the same temperature a solution of 8.0 g (0.020 mol) of 7-benzyl-8-(3-oxocyclopentyl)-1,3-dipropylpurine-2,6-dione in 70 ml of absolute tetrahydrofuran is added dropwise. The mixture is stirred for 2 hours at -70° C. and then for 2 hours at -30° C., then water is carefully added at -30° C. The phases are separated, the organic phase is evaporated down, the residue is taken up in dichloromethane, washed with water and the solution is dried and evaporated down. Purification is carried out by chromatography on silica gel using a mixture of cyclohexane/ethyl acetate as eluant in the ratio 3:1. 3.55 g (35.5% of theory) of the title compound are obtained in the form of a yellowish oil which crystallises when left to stand.

Workup

  1. customAt -75° C
  2. stirringThe mixture is stirred for 2 hours at -70° C.
  3. waitfor 2 hours at -30° C.
  4. customThe phases are separated
  5. customthe organic phase is evaporated down
  6. washwashed with water
  7. customthe solution is dried
  8. customevaporated down
  9. customPurification
  10. additiona mixture of cyclohexane/ethyl acetate as eluant in the ratio 3:1

Sources & evidence

ORD record
ord-e895dd3aaf744267b851878c7d1b172b
Source dataset
uspto-grants-1997_06
Patent number
US05641784

Reaction notes

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