N4-(4-methoxy-phenyl)-5-nitro-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4-diamine → N4-(4-methoxy-phenyl)-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4,5-triamine

HRID 1481247Notes

Reaction equation

HRID 1481247 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12]([NH:19][C:20]3[CH:21]=[N:22][N:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:24]=3)[N:11]=2)=[CH:5][CH:4]=1>C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][N:13]=[C:12]([NH:19][C:20]3[CH:21]=[N:22][N:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:24]=3)[N:11]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 89720564N4-(4-methoxy-phenyl)-5-nitro-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4-diamine

Product 1

HCID 89720507N4-(4-methoxy-phenyl)-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4,5-triamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 800 mg (1.98 mmol) N4-(4-Methoxy-phenyl)-5-nitro-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4-diamine in 20 ml THF is hydrogenated with 200 mg palladium on charcoal as catalyst at room temperature and under atmospheric pressure. The catalyst is filtered off; the filtrate is evaporated and dried under vacuum giving N4-(4-methoxy-phenyl)-N2-(1-phenyl-1H-pyrazol-4-yl)-pyrimidine-2,4,5-triamine as greenish crystals; HPLC/MS (A): 1.45 min, [M+H] 374;

Workup

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

Sources & evidence

ORD record
ord-cc6f93720eb149c7b6bc5675489417e6
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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