O-Cresol → HCID 69922894, compound

HRID 1005975Notes

Reaction equation

HRID 1005975 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].[C:19]1([CH3:26])[C:24]([OH:25])=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:25][C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:26])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 335O-CresolHCID 962WaterHCID 10796Cesium carbonateHCID 24903915Ethyl 4-chloro-2-(pyridin-4-yl)pyrimidine-5-carboxylate

Product 1

HCID 69922894HCID 69922894, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.6 g (2 28 mmol) 4-chloro-2-pyridin-4-yl-pyrimidine-5-carboxylic acid ethyl ester, 0.27 g (2 50 mmol) o-cresol and 2.97 g (9.10 mmol) Cs2CO3 in 15 ml acetonitrile was stirred for 17 h at RT. The suspension was poured into 150 ml H2O and extracted three times with 90 ml ethyl acetate. The combined organic phases were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, ethyl acetate/MeOH 100:1) to give 0.74 g (97%) 2-pyridin-4-yl-4-o-tolyloxy-pyrimidine-5-carboxylic acid ethyl ester as a yellow solid, MS (EI): 335.1 (M+).

Workup

  1. extractionextracted three times with 90 ml ethyl acetate
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, ethyl acetate/MeOH 100:1)

Sources & evidence

ORD record
ord-684454e98e464b15a1c725510b2679f4
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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