Allyl bromide → HCID 17961840, compound

HRID 1375550Notes

Reaction equation

HRID 1375550 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-9870b38eb0154a2f9f55276c744d485d
Source dataset
uspto-grants-2007_01
Patent number
US07169780B2

Reaction notes

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