Methanol → HCID 19047319, compound

HRID 1780767Notes

Reaction equation

HRID 1780767 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[O:10]1[CH:16]2[CH:11]1[CH:12]=[CH:13][CH2:14][CH2:15]2.CO>[Pd].O1CCCC1>[OH:10][CH:11]1[CH2:16][CH2:15][C:14]([N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])=[CH:13][CH2:12]1

Participants

6

Reactant 3

HCID 887MethanolHCID 1135ThymineHCID 1608667-Oxabicyclo[4.1.0]hept-2-ene

Product 1

HCID 19047319HCID 19047319, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6.3 g (50 mmol) of thymine are treated with 2 mol % of the palladium(0) catalyst prepared in situ as described above and with one equivalent of 3,4-epoxycyclohexene in tetrahydrofuran first at 0° C. and then for 4 hours at the reflux temperature. Methanol is added to the reaction mixture, the suspension is filtered, the filtrate is concentrated and the residue is chromatographed over silica gel using methylene chloride/methanol 20/1. 1.8 g (16.2% of theory) of 1-[(4RS)-4-hydroxy-cyclohex-1-en-1-yl]thymine of melting point 223° C. are obtained. 1H NMR (270 MHz, d6 -DMSO); δ[ppm]: 11.23 (s, 1H), 7.69 (s, 1H), 4.59 (m, 1H), 2.84 (t, 1H), 2.42-1.81 (m, 6H), 1.79 (s, 3H), 1.61 (m, 1H).

Workup

  1. customprepared in situ
  2. customfirst at 0° C.
  3. filtrationthe suspension is filtered
  4. concentrationthe filtrate is concentrated
  5. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-21c19f7a233c45f48e57d49008b757a2
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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