Potassium Carbonate → (S)-N1-((2,3-Dihydroxy)propyl)cytosine

HRID 232907Notes

Reaction equation

HRID 232907 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].[CH2:9]1[O:11][C@@H:10]1[CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:11][C@H:10]([CH2:12][OH:13])[CH2:9][N:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5460455(+)-GlycidolHCID 178418229Cytosine

Product 1

HCID 11805434(S)-N1-((2,3-Dihydroxy)propyl)cytosineYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of cytosine (2.2 g, 19.8 mmol) with (R)-glycidol (88% ee, 1.51 ml, 22.8 mmol) in the presence of anhydrous potassium carbonate (40 mg, 0.289 mmol) in dry DMF (20 ml) at 72° C. for 5 hours, as described in Example 1, furnished the title compound (88% ee) in 43.1% yield.

Sources & evidence

ORD record
ord-0d91becee4f14c64a252fcb6929bd28f
Source dataset
uspto-grants-1997_01
Patent number
US05591852

Reaction notes

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