Isobutyl iodide → 1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione

HRID 2205652Notes

Reaction equation

HRID 2205652 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][NH:4][C:3]1=[O:9].[CH2:10](I)[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:10]([N:4]1[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[C:3]1=[O:9])[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 10796Cesium carbonateHCID 790663-Methyluracil

Product 1

HCID 674157251-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-Methyluracil (3.0 g, 23.8 mmol), isobutyl iodide (7 mL, 60 mmol) and cesium carbonate (11.6 g, 35.7 mmol) in DMF (30 mL) is stirred at room temperature over a weekend. Solvent is removed under vacuum. The residue is treated with water, and then extracted with dichloromethane four times. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and then filtered through a short silica gel column. The filtrate is concentrated to dryness to give product as off white solids, which is used in the next step without further purification. MS (ESI) m/z 183.1 [M+H]+.

Workup

  1. customSolvent is removed under vacuum
  2. additionThe residue is treated with water
  3. extractionextracted with dichloromethane four times
  4. washThe combined organic phase is washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through a short silica gel column
  7. concentrationThe filtrate is concentrated to dryness
  8. customto give product as off white solids, which
  9. customis used in the next step without further purification

Sources & evidence

ORD record
ord-71f568db3e8f4e7bbbacaaf61828bbe4
Source dataset
uspto-grants-2016_06
Patent number
US09371327B2

Reaction notes

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