Dimethyl Sulfoxide → HCID 19047310, compound

HRID 1780762Notes

Reaction equation

HRID 1780762 reaction equation
[CH3:1][C:2]1[C:3]([NH2:9])=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.CS(C)=O.[O:14]1[C:16]2[CH2:17][CH2:18][CH2:19][C:15]1=2>[Pd].O1CCCC1>[NH2:9][C:3]1[C:2]([CH3:1])=[CH:7][N:6]([CH:18]2[CH2:19][CH:15]([OH:14])[CH:16]=[CH:17]2)[C:5](=[O:8])[N:4]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 22121731HCID 22121731, compoundHCID 178430896HCID 178430896, compound

Product 1

HCID 19047310HCID 19047310, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

50 g (0.4 mol) of 5-methylcytosine are added to a solution of the palladium(0) catalyst (1.6 mol %) prepared in situ as described above in 200 ml of dry tetrahydrofuran/200 ml of dry dimethylsulfoxide at 5° C. 49.2 g (0.6 mol) of epoxycyclopentene, dissolved in 100 ml of tetrahydrofuran, are added dropwise to this suspension, while stirring (1.5 hours). The mixture is stirred at room temperature for 3 days and then concentrated, and the residue is stirred with 2N sodium carbonate solution, filtered off and washed with water and acetone. 20.2 g (24.4% of theory) of 4-amino-5-methyl-1-[(1RS,4SR)-4-hydroxy-cyclopent-2-en-1-yl]pyrimidin-2(1H)-one of melting point 241°-245° C. are obtained. Chromatography (silica gel, methylene chloride/methanol 3/1) of the neutralized mother liquor gives, in addition to 5-methylcytosine (14.95 g, melting point 264°-269° C.) a further 9.87 g (11.9% of theory) of the title compound; total yield: 36.3% of theory. 1H NMR (270 MHz, d6 -DMSO); δ[ppm]: 7.23 (s, 1H), 7.12 (s, broad, 1H), 6.70 (s, broad, 1H), 6.09 (m, 1H), 5.74 (m, 1H), 5.45 (m, 1H), 5.17 (s, 1H), 4.61 (m, 1H), 2.71 (m, 1H), 1.81 (s, 3H), 1.27 (m, 1H).

Workup

  1. customprepared in situ
  2. additionare added dropwise to this suspension
  3. stirringThe mixture is stirred at room temperature for 3 days
  4. concentrationconcentrated
  5. stirringthe residue is stirred with 2N sodium carbonate solution
  6. filtrationfiltered off
  7. washwashed with water and acetone

Sources & evidence

ORD record
ord-3631cb4a220a4c79b2f3de3655e204e2
Source dataset
uspto-grants-1997_05
Patent number
US05631259

Reaction notes

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