Adenine → HCID 19047346, compound

HRID 1780764Notes

Reaction equation

HRID 1780764 reaction equation
P(OC(C)C)(OC(C)C)OC(C)C.C([Li])CCC.[N:19]1[C:27]([NH2:28])=[C:26]2[C:22]([N:23]=[CH:24][NH:25]2)=[N:21][CH:20]=1.[O:29]1[CH:35]2[CH:30]1[CH:31]=[CH:32][CH2:33][CH2:34]2>[Pd].CCCCCC.O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.CS(C)=O>[OH:29][CH:30]1[CH2:35][CH2:34][CH:33]([N:23]2[CH:24]=[N:25][C:26]3[C:22]2=[N:21][CH:20]=[N:19][C:27]=3[NH2:28])[CH:32]=[CH:31]1

Participants

11

Reactant 4

HCID 190AdenineHCID 8304Triisopropyl phosphiteHCID 1608667-Oxabicyclo[4.1.0]hept-2-eneHCID 178418339Butyllithium

Product 1

HCID 19047346HCID 19047346, compoundYield 36.9%

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

The palladium(0) catalyst is prepared by bringing together 179.6 mg of palladium(II) acetate, 2 ml of triisopropyl phosphite and 1.06 ml of a 1.4 molar solution of butyllithium in n-hexane in 60 ml of dry tetrahydrofuran at 0° C. under argon. 60 ml of dry dimethylsulfoxide and 17.32 g (0.128 mol) of adenine are then added. After stirring for 15 minutes, 12.3 g (0.128 mol) of 3,4-epoxycyclohexene, dissolved in 40 ml of dry tetrahydrofuran, are added dropwise (3 hours). The suspension is stirred at room temperature for 24 hours, poured into 650 ml of ethanol and stirred and the precipitate (1 g of adenine) is filtered off with suction. The filtrate is concentrated and the residue is chromatographed over aluminum oxide using methylene chloride/methanol 15/1. 7.96 g (36.9% of theory) of 9-[(1RS,4SR)-4-hydroxycyclohex-2-en-1-yl]adenine of melting point 181° to 183° C. are obtained. 1H NMR (270 MHz, d6 -DMSO); δ[ppm]: 8.15 (s, 1H), 8.04 (s, 1H), 7.22 (s, 2H), 6.09 (m, 1H), 5.84 (m, 1H), 5.06 (m, 1H), 4.93 (d, 1H), 4.09 (m, 1H), 1.99 (m, 2H), 1.81 (m, 1H),, 1.56 (m, 1H).

Workup

  1. customat 0° C.
  2. additionare added dropwise (3 hours)
  3. stirringThe suspension is stirred at room temperature for 24 hours
  4. stirringstirred
  5. filtrationthe precipitate (1 g of adenine) is filtered off with suction
  6. concentrationThe filtrate is concentrated
  7. customthe residue is chromatographed over aluminum oxide

Sources & evidence

ORD record
ord-6e14b0ec78f34ee0b298c7c757c73c4b
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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