2-Fluoro-4-nitrophenol → HCID 67523891, compound

HRID 659016Notes

Reaction equation

HRID 659016 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][OH:25])[N:16]=1>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:13][C:19]1[CH:20]=[CH:15][N:16]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][OH:25])[N:18]=1

Participants

5

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 24758Sodium hydrideHCID 86639105HCID 86639105, compound

Product 1

HCID 67523891HCID 67523891, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

358 mg (14.2 mmol) 95% sodium hydride was given to a solution of 2.12 g (13.5 mmol) 2-fluoro-4-nitrophenol in 25 ml DMF. Stirring was continued for 30 min. at room temperature. 2.53 g (13.5 mmol) 3-(4-Chloro-pyrimidin-2-ylamino)-propan-1-ol were added and the mixture heated to 140° C. for 24 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 material was purified by chromatography over silica (dichloromethane/ethanol 95:5) to give 2.92 g (70%) 3-[4-(2-fluoro-4-nitro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol as slightly yellow oil.

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. customThe obtained material was purified by chromatography over silica (dichloromethane/ethanol 95:5)

Sources & evidence

ORD record
ord-1e7b34c38c3e4c08b6500de677d98059
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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