N-methyl-4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine → 4-(2-(4-aminophenoxy)phenyl)-N-methylpyrimidin-2-amine

HRID 446288

Reaction equation

HRID 446288 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH:6]=[CH:5][N:4]=1.[H][H]>[Pd].CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:7]2[CH:6]=[CH:5][N:4]=[C:3]([NH:2][CH3:1])[N:8]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 66970416N-methyl-4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 585884984-(2-(4-aminophenoxy)phenyl)-N-methylpyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N-methyl-4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine (0.667 g, 2.1 mmol) and palladium, 10 wt. % on activated carbon, wet (0.44 g, 0.41 mmol) in a 100 mL round bottom flask was added MeOH under nitrogen via syringe. The atmosphere was replaced with hydrogen from a balloon and the mixture stirred rapidly for 24 h. The reaction was flushed with nitrogen, and filtered through celite rinsing with 100 mL MeOH. The filtrate was concentrated in vacuo to give 4-(2-(4-aminophenoxy)phenyl)-N-methylpyrimidin-2-amine as a light yellow solid. MS m/z=293 [M+1]+. Calc'd for C17H16N4O: 292.34.

Workup

  1. customThe reaction was flushed with nitrogen
  2. filtrationfiltered
  3. washthrough celite rinsing with 100 mL MeOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-13f841bbb72a4c0a893332c24ed008b6
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Linked notes

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