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

HRID 2274248Notes

Reaction equation

HRID 2274248 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-75d38fbdb9c64b6f8a1ee301f4194118
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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