Allyl bromide → HCID 86627797, compound

HRID 645511Notes

Reaction equation

HRID 645511 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:17][CH2:16][C:13]3([CH2:15][CH2:14]3)[CH2:12][CH2:11]2)[C:5]([C:18]([OH:20])=[O:19])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29]>CN(C=O)C.O>[CH2:29]([O:19][C:18]([C:5]1[C:6]([O:8][CH2:9][CH:10]2[CH2:11][CH2:12][C:13]3([CH2:15][CH2:14]3)[CH2:16][CH2:17]2)=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)=[O:20])[CH:28]=[CH2:27]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 866277982-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

Product 1

HCID 86627797HCID 86627797, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the 2-chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid (490 mg) in DMF (2.9 mL) are added K2CO3 (4.4 mmol) and allyl bromide (7.4 mmol) at room temperature. After stirring at 50° C. for 0.5 h, the reaction mixture is cooling and diluted with H2O. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified by silica gel column chromatography to give a crude title compound.

Workup

  1. temperaturethe reaction mixture is cooling
  2. extractionThe mixture is extracted with AcOEt
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4db417b787824fa787f8ffc9e151781f
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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