Sodium Hydroxide → 4-(2,4-dimethyl-1,3-thiazol-5-yl)-N-(4-fluorophenyl)pyrimidin-2-amine

HRID 47201Notes

Reaction equation

HRID 47201 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+]([O-])(O)=O.[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[CH:22][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:22]=[CH:21][C:20]([F:19])=[CH:25][CH:24]=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 1785125564-Fluorophenylguanidine nitrate

Product 1

HCID 65392864-(2,4-dimethyl-1,3-thiazol-5-yl)-N-(4-fluorophenyl)pyrimidin-2-amineYield 89.6%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1.0 mmol, 0.21 g) and N-(4-fluoro-phenyl)-guanidine nitrate (2.0 mmol, 0.44 g) in 2-methoxyethanol (5 mL) was added 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/PE, 2:1) and recrystallisation from EtOAc/PE to afford the title compound as brown crystals (269 mg, 89%). 1H-NMR (300 MHz, CDCl3) δ2.69 (s, 3H, CH3), 2.71 (s, 3H, CH3), 6.93 (d, 1H, J=5.3 Hz, pyrimidinyl-H), 7.03 (m, 2H, Ph-H), 7.58 (m, 2H, Ph-H), 8.40 (d, I H, J=5.3 Hz, pyrimidinyl-H).

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/PE, 2:1) and recrystallisation from EtOAc/PE

Sources & evidence

ORD record
ord-762c620c0b5a43e38736d27877524647
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Reaction notes

Loading…