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Cesium carbonate → Ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate

HRID 2284653
Notes
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Reaction equation

HRID 2284653 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][N:3]=1.Br[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([NH:1][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][N:3]=2)=[CH:19][CH:20]=1)#[N:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 12162Benzonitrile, 4-bromo-HCID 90052100Ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate

Product 1

HCID 90052034Ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylateYield 32.9%

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tris(dibenzylideneacetone)dipalladium(0) (1.14 g) and 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (1.45 g) in 1,4-dioxane (150 mL), ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate (C3, 5.61 g), 4-bromobenzonitrile (6.83 g) and cesium carbonate (24.40 g) were added at room temperature, and the mixture was stirred at 100° C. for 11 hours and 30 minutes under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, then the insoluble matter was removed by filtration through Cerite, and then 1.0 mol/L aqueous hydrochloric acid and ethyl acetate were added. The organic layer was separated, washed successively with 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate was added, and the solid matter was taken by filtration to obtain ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (C4, 2.68 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe insoluble matter was removed by filtration through Cerite
  3. addition1.0 mol/L aqueous hydrochloric acid and ethyl acetate were added
  4. customThe organic layer was separated
  5. washwashed successively with 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the obtained residue, ethyl acetate was added
  9. filtrationthe solid matter was taken by filtration

Sources & evidence

ORD record
ord-e492db74e3c947e6ac17c4bd427ab7fb
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145415B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes