Potassium Carbonate → HCID 22509303, compound

HRID 984876Notes

Reaction equation

HRID 984876 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][N:3]=1.[C:13]([C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:23]=1)[NH2:20])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>O>[C:24]([C:22]1[CH:21]=[C:19]([NH:20][C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][N:3]=2)[CH:18]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:23]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754193,5-Di-tert-butylanilineHCID 104878152-Chloro-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 22509303HCID 22509303, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 2-chloropyrimidine-5-carboxylate (335 mg), 3,5-di-tert-butylaniline (370 mg), and K2CO3 (600 mg) was heated at 110° C. After the disappearance of the materials was observed with TLC, the reaction mixture was poured into water, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and the solvent was evaporated. The residue was purified by silica gel flash column chromatography (n-hexane: AcOEt=10:1) to give white crystals of ethyl 2-[N-(3,5-di-tert-butylphenyl)amino]pyrimidine-5-carboxylate (574 mg, 90%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel flash column chromatography (n-hexane: AcOEt=10:1)

Sources & evidence

ORD record
ord-7e4ed6b11c3048eaa311080f6a7276d1
Source dataset
uspto-grants-2005_03
Patent number
US06869959B1

Reaction notes

Loading…