Nitrofungin → HCID 67523903, compound

HRID 659009Notes

Reaction equation

HRID 659009 reaction equation
[H-].[Na+].[Cl: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>[Cl: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 12074NitrofunginHCID 24758Sodium hydrideHCID 86639105HCID 86639105, compound

Product 1

HCID 67523903HCID 67523903, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

370 mg (14.7 mmol) sodium hydride was given to a solution of 2.31 g (13.3 mmol) 2-chloro-4-nitrophenol in 25 ml DMF. Stirring was continued for 30 min. at room temperature. 2.50 g (13.3 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 dissolved in 3 ml dichloromethane and purified by chromatography over silica (dichloromethane/ethanol 95:5) to give 2.92 g (67%) 3-[4-(2-chloro-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 material was dissolved in 3 ml dichloromethane
  7. custompurified by chromatography over silica (dichloromethane/ethanol 95:5)

Sources & evidence

ORD record
ord-747279c928104cbbaffe30bd51801587
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

Loading…