(2-Chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine → 2-Chloro-N4-(4-methoxyphenyl)pyrimidine-4,5-diamine

HRID 1481248Notes

Reaction equation

HRID 1481248 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([N+:17]([O-])=O)=[CH:4][N:3]=1>C1COCC1.[Ni]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[C:5]([NH2:17])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 89717635(2-Chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine

Product 1

HCID 897194042-Chloro-N4-(4-methoxyphenyl)pyrimidine-4,5-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.86 g (6.64 mmol) (2-chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine (from example 1) in 20 ml THF is hydrogenated with 1.0 g sponge-nickel as catalyst at room temperature and under atmospheric pressure. The catalyst is filtered off; the filtrate is evaporated and dried under vacuum giving 2-chloro-N4-(4-methoxy-phenyl)-pyrimidine-4,5-diamine as grey solid; HPLC/MS (A): 1.63 min, [M+H] 251;

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-e1db04ef757942e2aecf035dc70ab71f
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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