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

HRID 1860461Notes

Reaction equation

HRID 1860461 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) δ 2.71 (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-b1ee8aecea3f4e22b77b54c6812a4798
Source dataset
uspto-grants-2003_03
Patent number
US06531479B2

Reaction notes

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