Thymine → 1-Benzyl-5-methyl-1H-pyrimidine-2,4-dione

HRID 342530Notes

Reaction equation

HRID 342530 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:10]([N:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1135ThymineHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 2379531-Benzyl-5-methyl-1H-pyrimidine-2,4-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of thymine (7.68 g, 61 mmol), benzyl bromide (10.55 g, 61 mmol), potassium carbonate (17.05 g, 123 mmol) and DMF (90 mL) was stirred 12 hours at 25° C. The reaction mixture was poured into water (500 mL) and extracted with ethyl acetate (3×200 mL). The combined extract was washed with water (5×100 mL), dried (Na2SO4) and concentrated in vacuo. The residue was crystallized from hexane/ethyl acetate to give 1-benzyl-5-methyl-2,4(1H,3H)-pyrimidinedione (9.4 g, 43.9 mmol), m.p. 170°-173° C.

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. extractionThe combined extract
  3. washwas washed with water (5×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-9e488b4fe38a4199b4b8b8c7a73d33ee
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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