Tetrahydrofuran → 1-[(1RS,4SR)-4-hydroxycyclopent-2-en-1-yl]cytosine

HRID 1780760Notes

Reaction equation

HRID 1780760 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].[O:9]1[C:11]2[CH2:12][CH2:13][CH2:14][C:10]1=2.O1CCCC1>[Pd].CS(C)=O>[OH:9][CH:10]1[CH2:14][CH:13]([N:1]2[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]2=[O:3])[CH:12]=[CH:11]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 22121731HCID 22121731, compoundHCID 178418229Cytosine

Product 1

HCID 190473311-[(1RS,4SR)-4-hydroxycyclopent-2-en-1-yl]cytosineYield 79.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

52.5 g (0.47 mol) of cytosine are reacted with 38.5 g (0.47 mol) of epoxycyclopentene at 0° C., by slow addition, in a mixture of in each case 220 ml of dry tetrahydrofuran and dimethylsulfoxide with 1 mol % of the palladium(0) catalyst prepared in situ as described above under an inert argon atmosphere. The reaction mixture is stirred at room temperature for 90 hours and then freed from the solvent and the residue is chromatographed over silica gel using methylene chloride/methanol 7/3. 71.8 g (79.2% of theory) of 1-[(1RS,4SR)-4-hydroxycyclopent-2-en-1-yl]cytosine of melting point 241°-242° C. are obtained. 1H-NMR (270 MHz, d6 -DMSO), δ[ppm]: 7.42 (d, 1H), 7.02 (s, 2H), 6.09 (m, 1H), 5.75 (m, 1H), 5.72 (d, 1H), 5.44 (m, 1H), 5.18 (d, 1H), 4.63 (m, 1H), 2.72 (m, 1H), 1.27 (m, 1H).

Workup

  1. customprepared in situ
  2. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-f3f413b7f4d24a74988e6718f99f5eee
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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