4-(2-Fluoro-4-nitrophenoxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine → 4-(5-Methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3-fluorobenzenamine

HRID 500761Notes

Reaction equation

HRID 500761 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:6]2[N:13]([CH3:14])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1>CC(O)=O.C(Cl)Cl.[Fe]>[CH3:14][N:13]1[C:6]2[C:5]([O:4][C:3]3[CH:15]=[CH:16][C:17]([NH2:19])=[CH:18][C:2]=3[F:1])=[N:10][CH:9]=[N:8][C:7]=2[CH:11]=[CH:12]1

Participants

5

Reactant 1

HCID 594245774-(2-Fluoro-4-nitrophenoxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 594245884-(5-Methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3-fluorobenzenamineYield 53.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-5-methyl-5H-pyrrolo[3,2-d] pyrimidine (29) (253.6 mg, 0.879 mmol) in AcOH (3 mL) at 90° C. was added iron powder (245 mg, 4.4 mmol). The mixture was stirred vigorously for 10 min and filtered. The filtrate was concentrated under reduced pressure to produce a solid, which was dissolved in DCM. The resultant solution was washed with cold NaHCO3 solution and water, dried over Na2SO4 and concentrated to provide a residue which was purified by column chromatography (eluent MeOH—CH2Cl2 1:20) to afford the title compound 30 as a brown solid (120.6 mg, 53% yield). LRMS (M+1) 240.1 (100%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto produce a solid, which
  4. washThe resultant solution was washed with cold NaHCO3 solution and water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto provide a residue which
  8. customwas purified by column chromatography (eluent MeOH—CH2Cl2 1:20)

Sources & evidence

ORD record
ord-123691c414614923b6f53bbb0a759a74
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

Loading…