Water → N4-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-iodopyrimidine-4,5-diamine

HRID 1926034Notes

Reaction equation

HRID 1926034 reaction equation
[NH2:1][C:2]1[C:3]([I:9])=[N:4][CH:5]=[N:6][C:7]=1I.[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[NH2:14].O>CN1CCCC1=O>[Cl:10][C:11]1[CH:12]=[C:13]([NH:14][C:7]2[C:2]([NH2:1])=[C:3]([I:9])[N:4]=[CH:5][N:6]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 118101544,6-Diiodopyrimidin-5-amine

Product 1

HCID 86615762N4-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-iodopyrimidine-4,5-diamineYield 81%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-amino-4,6-diiodopyrimidine (3.83 g) and 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (2.78 g) in 1-methyl-2-pyrrolidone (30 mL) was stirred at 70° C. for 14 hrs. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by column chromatography (eluent, ethyl acetate:hexane=1:4→2:3→1:1) to give the title compound (4.21 g) as brown powder crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was separated
  6. custompurified by column chromatography (eluent, ethyl acetate:hexane=1:4→2:3→1:1)

Sources & evidence

ORD record
ord-b324adb33e75410d82d94399c469ee06
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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