Allyl bromide → HCID 17961840, compound

HRID 1351362Notes

Reaction equation

HRID 1351362 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-cf3cb0c21bd84abe9effe1a179937574
Source dataset
uspto-grants-2007_05
Patent number
US07217713B2

Reaction notes

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