4,6-Dichloro-5-nitro-2-phenylpyrimidine → 4,6-Dichloro-2-phenylpyrimidin-5-amine

HRID 1905842Notes

Reaction equation

HRID 1905842 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([Cl:11])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1>CCOCC.C([O-])(=O)C.[Ni]>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][C:6]=1[Cl:11]

Participants

4

Reactant 1

HCID 1006444,6-Dichloro-5-nitro-2-phenylpyrimidine

Product 1

HCID 7366734,6-Dichloro-2-phenylpyrimidin-5-amineYield 72.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226428Ether acetateSolvent

Procedure

27.0 g of 4,6-dichloro-5-nitro-2-phenylpyrimidine are hydrogenated in ether acetate at room temperature by treatment with Raney nickel. The catalyst is afterwards separated and the reaction solution is concentrated by evaporation. Crystallisation of the residue from petroleum ether then yields 17.4 g of 5-amino-4,6-dichloro-2-phenylpyrimidine, m.p. 143°-144° C. (compound No. 1).

Workup

  1. customThe catalyst is afterwards separated
  2. concentrationthe reaction solution is concentrated by evaporation
  3. customCrystallisation of the residue from petroleum ether

Sources & evidence

ORD record
ord-0585826f0ec546e39554c0e3decd9b03
Source dataset
uspto-grants-1987_03
Patent number
US04648896

Reaction notes

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