Ethyl acetate hexane → N4-(3-aminophenyl)-5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)pyrimidine-2,4-diamine

HRID 1482665Notes

Reaction equation

HRID 1482665 reaction equation
[F:1][C:2]1[C:3]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[H][H].CCCCCC.C(OCC)(=O)C>CO.[Pd]>[NH2:29][C:25]1[CH:24]=[C:23]([NH:22][C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:11][CH:10]=3)[N:4]=2)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 867243285-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamineHCID 178418361HCID 178418361, compound

Product 1

HCID 86724329N4-(3-aminophenyl)-5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)pyrimidine-2,4-diamineYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of Pd/C (0.2 g) in methanol (20 mL), 5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamine (0.40 g) was added under nitrogen atmosphere into the autoclave at room temperature. Hydrogen pressure (70 psi) was applied and the reaction mixture was stirred overnight at room temperature. The reaction was monitored on TLC using hexane:ethyl acetate (4:6) as mobile phase. After completion, the reaction mixture was filtered using Celite and the filter cake was washed with methanol. The combined filtrate was concentrated under reduced pressure at 40° C. to give 0.3 g of N4-(3-aminophenyl)-5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)pyrimidine-2,4-diamine as a solid.

Workup

  1. additionwas added under nitrogen atmosphere into the autoclave at room temperature
  2. filtrationAfter completion, the reaction mixture was filtered
  3. washthe filter cake was washed with methanol
  4. concentrationThe combined filtrate was concentrated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-7f3e97ce688c461ab2b9fabbbd30332f
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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