Water → 6-Chloro-3-methyl-1-propyl-2,4(1H,3H)-pyrimidinedione

HRID 131571

Reaction equation

HRID 131571 reaction equation
[Cl:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH2:18][CH3:19].O>CN(C=O)C>[Cl:1][C:2]1[N:7]([CH2:17][CH2:18][CH3:19])[C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 961416-chloro-3-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 8169336-Chloro-3-methyl-1-propyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-chloro-3-methyl uracil (10 g) and potassium carbonate (10.34 g) in DMF (70 ml) under nitrogen was treated with n-propyl iodide (25.4 g) and heated at reflux for 8 h. The reaction 30 was cooled and then poured into water (700 ml) and extracted with ethyl acetate. The combined organics were dried and evaporated in vacuo to afford the subtitle compound an orange oil, 17.52 g. δ 1HCDCl3 0.98 (3H, t), 1.74 (2H, sextet), 3.33 (3H, s), 4.02 (2H, t), 8.02 (1H, s).

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 h
  3. customThe reaction 30
  4. temperaturewas cooled
  5. extractionextracted with ethyl acetate
  6. customThe combined organics were dried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-123c4983d1f349798e70b6e416ec6dbf
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Linked notes

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