4-Methylsulfanyl-6-(4-nitro-phenoxy)-pyrimidine → 4-(6-Methylsulfanyl-pyrimidin-4-yloxy)-phenylamine

HRID 659027Notes

Reaction equation

HRID 659027 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[N:6]=[CH:5][N:4]=1>C(O)C.C1COCC1.[Pd]>[CH3:1][S:2][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH:8]=1

Participants

4

Reactant 1

HCID 675239294-Methylsulfanyl-6-(4-nitro-phenoxy)-pyrimidine

Product 1

HCID 675239014-(6-Methylsulfanyl-pyrimidin-4-yloxy)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 4-methylsulfanyl-6-(4-nitro-phenoxy)-pyrimidine (0.5 g, 1.9 mmol) in ethanol/THF (25 ml, 1:1) is added catalyst (10% Pd/C, 0.3 g, 0.28 mmol). The starting material is hydrogenated at 4 bar for 4 h at r.t. The catalyst is filtered off and the solvent is removed. Due to instability, the product is used without any further purification for the subsequent reaction.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed
  3. customDue to instability, the product is used without any further purification for the subsequent reaction

Sources & evidence

ORD record
ord-2c7650bacd224ed498aae6791f0ed950
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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