Sodium Hydroxide → 4-[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-2-nitro-phenol

HRID 47205Notes

Reaction equation

HRID 47205 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[S:4][C:3]=1/[CH:8]=[CH:9]/[C:10](N(C)C)=O.[N+:15]([O-:18])(O)=[O:16].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[C:22]([N+]([O-])=O)[CH:21]=1.[OH-].[Na+]>COCCO>[CH3:7][C:5]1[S:4][C:3]([C:8]2[CH:9]=[CH:10][N:29]=[C:27]([NH:26][C:23]3[CH:24]=[CH:25][C:20]([OH:19])=[C:21]([N+:15]([O-:18])=[O:16])[CH:22]=3)[N:28]=2)=[C:2]([CH3:1])[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneHCID 178512576HCID 178512576, compound

Product 1

HCID 99026544-[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-2-nitro-phenolYield 17.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

3-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1 mmol, 0.21 g) in 2-methoxyethanol (5 mL ) was treated with N-(4-hydroxy-2-nitro-phenyl)-guanidine nitrate (2 mmol, 0.52 g) in the presence of NaOH (40 mg). The reaction mixture was refluxed under N2 for 24 h. The solvent was evaporated to dryness and the residue was purified by flash chromatography (EtOAc) and recrystallisation from EtOAc/PE to afford the title compound as a yellow powder (61 mg). 1H-NMR (300 MHz, CDCl3) δ2.71 (s, 3H, CH3), 2.73 (s, 3H, CH3), 7.01 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.18 (m, 1H, Ph-H), 7.64 (m, 1H, Ph-H), 8.42 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.75 (d, 1H, J=2.7 Hz, Ph-H), 10.45 (br. s, 1H, OH).

Workup

  1. temperatureThe reaction mixture was refluxed under N2 for 24 h
  2. customThe solvent was evaporated to dryness
  3. customthe residue was purified by flash chromatography (EtOAc) and recrystallisation from EtOAc/PE

Sources & evidence

ORD record
ord-17c1f8bc81c7456fb53804e3a92f4fd5
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Reaction notes

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