Potassium Carbonate → 1-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-uracil

HRID 908528Notes

Reaction equation

HRID 908528 reaction equation
CC1(C)[O:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]2[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]2=[O:17])[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+]>Cl>[OH:3][CH2:4][CH:5]([CH2:6][OH:7])[CH2:8][CH2:9][N:10]1[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]1=[O:17]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 578389791-[2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl]uracil

Product 1

HCID 2896501-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-uracilYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of compound 34 (60 g, 0.239 mol) in 1N HCl (450 mL) was heated to 110° C. for 30 min. The reaction mixture was cooled, carefully neutralized with potassium carbonate to pH=7 and concentrated under vacuum. The residue was passed through small column using 20% methanol in chloroform to give the title compound (45 g, 88%) as a thick liquid. TLC: Chloroform/Methanol, 6:4, Rf=0.2

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aab967587c89465f8567c8afecdd70a6
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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