Methylurea → 1,6-Dimethyluracil

HRID 60339

Reaction equation

HRID 60339 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[O:4].[CH2:6]=[C:7]1[O:10][C:9](=O)[CH2:8]1>CO>[CH3:1][N:2]1[C:7]([CH3:6])=[CH:8][C:9](=[O:10])[NH:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 11719MethylureaHCID 12661Diketene

Product 1

HCID 106068181,6-DimethyluracilYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-methylurea (30 g, 0.356 mol) in 4-methyleneoxetan-2-one (26.4 g, 0.356 mol) was heated at 100° C. for 18 h, cooled to RT then diluted with MeOH (50 mL). The reaction was filtered and the filtered solid was washed with MeOH (20 mL) and dried to give 1,6-dimethylpyrimidine-2,4(1H,3H)-dione (9 g, 18% yield) as a white solid. 1H NMR (CDCl3) δ: 8.33 (s, 1H), 5.58 (s, 1H), 3.38 (s, 3H), 2.26 (s, 3H). LCMS: MH+ 141 and TR=0.368 min. Used without further purification.

Workup

  1. filtrationThe reaction was filtered
  2. washthe filtered solid was washed with MeOH (20 mL)
  3. customdried

Sources & evidence

ORD record
ord-3676721470164f839a71b8ed5c811bf2
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Linked notes

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