Hydrochloric Acid → N-(2-(Hydroxyethoxy)methyl)-5-methyluracil

HRID 1078570Notes

Reaction equation

HRID 1078570 reaction equation
C([O:4][CH2:5][CH2:6][O:7][CH2:8][N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11])(=O)C.O(C)[Na].Cl>CO>[OH:4][CH2:5][CH2:6][O:7][CH2:8][N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 50788751-[(2-Acetoxyethoxy)Methyl]ThymineHCID 178418582HCID 178418582, compound

Product 1

HCID 72358N-(2-(Hydroxyethoxy)methyl)-5-methyluracilYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 1-[(2-acetoxyethoxy)methyl]thymine (4 g, 16 mmol) in CH3OH (100 mL) was added NaOCH3 in CH3OH (20 mL, 1N). After 2 hours of stirring at room temperature, 1N HCl was added to adjust the pH to 4.0. Methanol and water were removed under vacuum to obtain a solid. The solid was dissolved in CH3OH and crystallized by dropwise addition of CHCl3; it was used in the next reaction without further purification. Yield 76%; Wt. 2.5 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 1.75 (s, CH3 C5 thymine), 3.55-3.75 (A2B2 pattern, O CH2 CH2 O), 5.10 (s, O CH2 N), 7.55 (s, H C6 thymine), 11.3 (s, HN thymine).

Workup

  1. customMethanol and water were removed under vacuum
  2. customto obtain a solid
  3. customcrystallized by dropwise addition of CHCl3
  4. customit was used in the next reaction without further purification

Sources & evidence

ORD record
ord-dc7852811672411c9823cf241e6016f4
Source dataset
uspto-grants-1996_08
Patent number
US05550132

Reaction notes

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