4-Nitrophenol → HCID 67524185, compound

HRID 658994Notes

Reaction equation

HRID 658994 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[N:15]=1>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:18]2[CH:19]=[CH:14][N:15]=[C:16]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[N:17]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 86639105HCID 86639105, compound

Product 1

HCID 67524185HCID 67524185, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

1.37 g (54.3 mmol) sodium hydride was given to a solution of 7.19 g (51.7 mmol) 4-nitrophenol in 97 ml DMF. Stirring was continued for 30 min. at room temperature. 9.70 g (51.7 mmol) 3-(4-Chloro-pyrimidin-2-ylamino)-propan-1-ol was added and the mixture heated to 140° C. for 15 h. The reaction mixture was evaporated, taken up with water and extracted with dichloromethane. The organic phase was extracted with sodium carbonate solution, dried (sodium sulphate) and evaporated. The obtained yellow oil (11 g) was dissolved in 10 ml dichloromethane and purified by chromatography over silica (ethyl acetate) to give 8.66 g (58%) 3-[4-(4-Nitro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with dichloromethane
  3. extractionThe organic phase was extracted with sodium carbonate solution
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. dissolutionThe obtained yellow oil (11 g) was dissolved in 10 ml dichloromethane
  7. custompurified by chromatography over silica (ethyl acetate)

Sources & evidence

ORD record
ord-3ed08bed646f446bb1699787e6d032b8
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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