HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Allyl bromide → 2-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

HRID 645511
Notes
Print preview

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 866277972-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07704996B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes