Methanol → HCID 135427632, compound

HRID 1780766Notes

Reaction equation

HRID 1780766 reaction equation
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].[O:12]1[CH:18]2[CH:13]1[CH:14]=[CH:15][CH2:16][CH2:17]2.CO>[Pd].O1CCCC1>[OH:12][CH:13]1[CH2:18][CH2:17][CH:16]([N:6]2[CH:7]=[N:8][C:9]3[C:10](=[O:11])[NH:1][C:2]([NH2:3])=[N:4][C:5]2=3)[CH:15]=[CH:14]1

Participants

6

Reactant 3

HCID 887MethanolHCID 1608667-Oxabicyclo[4.1.0]hept-2-eneHCID 135398634Guanine

Product 1

HCID 135427632HCID 135427632, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7.56 g (50 mmol) of guanine are reacted with 2 mol % of the palladium(0) catalyst prepared in situ as above and one equivalent of 3,4-epoxycyclohexene in tetrahydrofuran first at 0° C. and then for 8 hours under reflux temperature, and the mixture is then poured into methanol. The reaction mixture is concentrated and the residue is taken up in 2-propanol and filtered off with suction. The residue is recrystallized first from ethanol with active charcoal and then from water. 3.1 g (25.1% of theory) of 9-[(1RS,4SR)-4-hydroxy-cyclohex-2-en-1-yl]guanine of melting point >300° C. are obtained. 1H NMR (270 MHz, d6 -DMSO); δ[ppm]: 10.57 (s, 1H), 7.60 (s, 1H), 6.46 (s, 2H), 6.05 (m, 1H), 5.77 (m, 1H), 4.91 (d, 1H), 4.79 (m, 1H), 4.06 (m, 1H), 1.95-1.75 (m, 3H), 1.53 (m, 1H).

Workup

  1. temperaturefor 8 hours under reflux temperature
  2. concentrationThe reaction mixture is concentrated
  3. filtrationfiltered off with suction
  4. customThe residue is recrystallized first from ethanol with active charcoal

Sources & evidence

ORD record
ord-d5b2880797f74a08a7cbbba9fab2e5b9
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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