Methanol → 4-(4-Aminophenoxy)pyrimidin-2-amine

HRID 1010374Notes

Reaction equation

HRID 1010374 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:5]=[C:4]([NH2:18])[N:3]=1.CO.O1CCCC1.C(OCC)(=O)C>[OH-].[Pd+2].[OH-].[C].CCCCCC>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:7]=[CH:2][N:3]=[C:4]([NH2:18])[N:5]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 6766744-Chloro-6-(4-nitrophenoxy)pyrimidin-2-amine

Product 1

HCID 229363964-(4-Aminophenoxy)pyrimidin-2-amineYield 340.9%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8058HexaneSolvent

Procedure

After suspending 4-chloro-6-(4-nitrophenoxy)pyrimidin-2-ylamine (1.60 g, 1.32 mmol) in a methanol (30 ml)—tetrahydrofuran (30 ml) mixed solvent, palladium hydroxide-carbon (300 mg) was added and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere. The catalyst was filtered off by celite filtration, and after washing with ethanol, the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=3:1), and the fraction containing the target substance was concentrated to obtain the title compound (910 mg, 4.50 mmol, 75%) as colorless crystals.

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off by celite filtration
  3. washafter washing with ethanol
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-b4887f992b0243e2869412a93dd412df
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

Loading…