Thiophene → 4-(3-Aminophenyl)-2-pyrimidinamine

HRID 269735Notes

Reaction equation

HRID 269735 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.S1C=CC=C1>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 27353824-(3-nitrophenyl)pyrimidin-2-amine

Product 1

HCID 552507314-(3-Aminophenyl)-2-pyrimidinamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(3-amino-phenyl)-pyrimidin-2-ylamine was prepared in an analogous manner: A solution of 4-(3-nitro-phenyl)-pyrimidin-2-ylamine (0.046 mol) in MeOH (250 ml) was hydrogenated at 50° C. with Pd/C 10% (2 g) as a catalyst in the presence of a solution of thiophene in DIPE (4% v/v, 1 ml). After uptake of H2 (3 equiv.), the catalyst was filtered off and the filtrate was concentrated and dried (vacuum 60° C.). Yield: 8.64g of 4-(3-amino-phenyl)-pyrimidin-2-ylamine (87%) (m.p.; 190-194° C.).

Workup

  1. filtrationAfter uptake of H2 (3 equiv.), the catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customdried (vacuum 60° C.)

Sources & evidence

ORD record
ord-5c3def6ff28d4b578f26e39476d8db1a
Source dataset
uspto-grants-2008_11
Patent number
US07449465B2

Reaction notes

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