Water → 2-(3-Ethyl-ureido)-7-pyrimidin-5-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

HRID 2112941Notes

Reaction equation

HRID 2112941 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8](Br)[CH:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+].[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1.O>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8]([C:31]2[CH:32]=[N:27][CH:28]=[N:29][CH:30]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 576430687-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 688364172-(3-Ethyl-ureido)-7-pyrimidin-5-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 7-bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (0.548 g, 1.54 mmol/prepared as in Example 6, Step 4) sodium acetate (0.63 g, 7.68 mmol), dppf (86 mg, 0.155 mmol), pyrimidine-5-boronic acid (0.289 g, 2.33 mmol) in toluene (30 mL)/water (6 mL)/ethanol (6 mL) was purged with nitrogen. PdCl2(PhCN)2 (60 mg, 0.156 mmol) was added and the mixture was purged with nitrogen then refluxed for 0.5 h. The reaction mixture was cooled and the resulting crystalline product was filtered and washed with water. The product was dissolved in hot methanol, filtered through celite and cooled to give 2-(3-ethyl-ureido)-7-pyrimidin-5-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester as a solid. ACPI-MS Found: [M+H]+=356.

Workup

  1. customwas purged with nitrogen
  2. customthe mixture was purged with nitrogen
  3. temperaturethen refluxed for 0.5 h
  4. temperatureThe reaction mixture was cooled
  5. filtrationthe resulting crystalline product was filtered
  6. washwashed with water
  7. dissolutionThe product was dissolved in hot methanol
  8. filtrationfiltered through celite
  9. temperaturecooled

Sources & evidence

ORD record
ord-1d96d72e4c5347b48c4277ee3dffecb4
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

Loading…