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

HRID 387987Notes

Reaction equation

HRID 387987 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-].[C+4].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].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 178420936HCID 178420936, 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-carbon hydroxide (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-c4643e1f18dc4f2196f740474861d2e1
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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