4-[[4-(4-Cyano-2,6-dimethylphenoxy)-5-nitro-2-pyrimidinyl]amino]benzonitrile → 4-[5-Amino-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrile

HRID 1294438Notes

Reaction equation

HRID 1294438 reaction equation
[C:1]([C:3]1[CH:27]=[C:26]([CH3:28])[C:6]([O:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]([NH:17][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[N:9]=2)=[C:5]([CH3:29])[CH:4]=1)#[N:2]>O1CCCC1.[Pd]>[NH2:14][C:13]1[C:8]([O:7][C:6]2[C:26]([CH3:28])=[CH:27][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[CH3:29])=[N:9][C:10]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 4863944-[[4-(4-Cyano-2,6-dimethylphenoxy)-5-nitro-2-pyrimidinyl]amino]benzonitrile

Product 1

HCID 4863954-[5-Amino-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrileYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[[4-(4-cyano-2,6-dimethylphenoxy)-5-nitro-2-pyrimidinyl]amino]-benzonitrile (0.0005 mol) in tetrahydrofuran (20 ml) was hydrogenated overnight with Pd/C 10% (0.100 g) as a catalyst. After uptake of H2 (3 equiv; 0.0015 mol), the catalyst was filtered off and the filtrate was concentrated by rotary evaporation and dried in vacuo over 16 hours at 40° C., yielding 0.15 g of 4-[[5-amino-4-(4-cyano-2,6-dimethylphenoxy)-2-pyrimidinyl]amino]benzonitrile (84%); mp.>300° C.

Workup

  1. filtrationAfter uptake of H2 (3 equiv; 0.0015 mol), the catalyst was filtered off
  2. concentrationthe filtrate was concentrated by rotary evaporation
  3. customdried in vacuo over 16 hours at 40° C.

Sources & evidence

ORD record
ord-92918773b99042499b83d534b94ef519
Source dataset
uspto-grants-2007_07
Patent number
US07241458B1

Reaction notes

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