HCID 22121731, compound → 1-[(1RS,4SR)-4-hydroxy-cyclopent-2-en-1-yl]-5-methyl-4-(1,2,4-triazol-1-yl)-pyrimidin-2(1H)-one

HRID 1780761Notes

Reaction equation

HRID 1780761 reaction equation
[O:1]1[C:3]2[CH2:4][CH2:5][CH2:6][C:2]1=2.[CH3:7][C:8]1[C:9]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)=[N:10][C:11](=[O:14])[NH:12][CH:13]=1>O1CCCC1.CS(C)=O.[Pd]>[OH:1][CH:3]1[CH2:4][CH:5]([N:12]2[CH:13]=[C:8]([CH3:7])[C:9]([N:15]3[CH:19]=[N:18][CH:17]=[N:16]3)=[N:10][C:11]2=[O:14])[CH:6]=[CH:2]1

Participants

6

Reactant 2

HCID 22121731HCID 22121731, compoundHCID 178430897HCID 178430897, compound

Product 1

HCID 190473051-[(1RS,4SR)-4-hydroxy-cyclopent-2-en-1-yl]-5-methyl-4-(1,2,4-triazol-1-yl)-pyrimidin-2(1H)-oneYield 25.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The equivalent amount of epoxycyclopentene is slowly added at 0° C. to 3.54 g (0.020 mol) of 5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (prepared by reaction of thymine with 1,2,4-triazole/POCl3 /triethylamine) in a mixture of 40 ml of dry tetrahydrofuran and 20 ml of dry dimethylsulfoxide with 5 mol % of the palladium(0) catalyst prepared in situ as above, and the reaction mixture is stirred at room temperature for 12 hours. The resulting suspension is filtered, the filtrate is concentrated and the residue is chromatographed over silica gel using methylene chloride/methanol 9/1. 1.34 g (25.8% of theory) of 1-[(1RS,4SR)-4-hydroxy-cyclopent-2-en-1-yl]-5-methyl-4-(1,2,4-triazol-1-yl)-pyrimidin-2(1H)-one (Example 1.18.1.) of melting point 198° to 204° C. are obtained. 1H NMR (270 KHz, d6 -DMSO), δ[ppm]: 9.31 (s, 1H), 8.38 (s, 1H), 8.07 (s, 1H), 6.25 (m, 1H), 5.92 (m, 1H), 5.52 (m, 1H), 5.28 (d, 1H), 4.71 (m, 1H), 2.87 (m, 1H), 2.30 (s, 3H), 1.47 (m, 1H).

Workup

  1. customprepared in situ as above, and the reaction mixture
  2. filtrationThe resulting suspension is filtered
  3. concentrationthe filtrate is concentrated
  4. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-fbd4497a3b0f42c9919f041b62dbeb0d
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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