Allyl bromide → HCID 17961840, compound

HRID 2114778Notes

Reaction equation

HRID 2114778 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[C:3]([O:5][C:6]1[CH:11]([OH:12])[NH:10][CH:9]=[N:8][C:7]=1[C:13]([O:15][CH3:16])=[O:14])=[O:4].[CH2:19](Br)[CH:20]=[CH2:21].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH2:21]([N:10]1[C:11](=[O:12])[C:6]([O:5][C:3](=[O:4])[C:2]([CH3:18])([CH3:17])[CH3:1])=[C:7]([C:13]([O:15][CH3:16])=[O:14])[N:8]=[CH:9]1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 178498974HCID 178498974, compound

Product 1

HCID 17961840HCID 17961840, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-[(2,2-dimethylpropanoyl)oxy]-6-hydroxy-1,6-dihydropyrimidine-4-carboxylate (see Example 4, Step 3) was dissolved in THF, then allyl bromide (2 eq.) and Cs2CO3 (2 eq.) were added. The reaction mixture was refluxed for 2 H, then evaporated. The residue was diluted with EtOAc, washed with 1N HCl, dried (Na2SO4) and the solvent evaporated. The product was purified by flash chromatography on silica gel eluting with a gradient of petroleum ether/EtOAc.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 H
  2. customevaporated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with 1N HCl
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customThe product was purified by flash chromatography on silica gel eluting with a gradient of petroleum ether/EtOAc

Sources & evidence

ORD record
ord-8298e9b72b884c4d9347eff6052eca4e
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

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