Sodium Hydroxide → (2,4-Difluoro-phenyl)-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-amine

HRID 47203Notes

Reaction equation

HRID 47203 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]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[NH:27][C:28]([NH2:30])=[NH:29].[OH-].[Na+]>COCCO>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[NH:27][C:28]1[N:30]=[C:8]([C:3]2[S:4][C:5]([CH3:7])=[N:6][C:2]=2[CH3:1])[CH:9]=[CH:10][N:29]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneHCID 178512554HCID 178512554, compound

Product 1

HCID 10336016(2,4-Difluoro-phenyl)-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-amineYield 79%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1.0 mmol, 0.21 g) and N-(2,4-difluoro-phenyl)-guanidine nitrate (2 mmol, 0.47 g) in 2-methoxyethanol (5 mL) was treated with NaOH (40 mg). After 24 h refluxing under N2 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 a brown powder (250 mg, 79%). 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), 7.01 (m, 2H, Ph-H), 7.58 (m, 2H, Ph-H), 8.40 (d, 1H, J=5.3 Hz, pyrimidinyl-H).

Workup

  1. temperatureAfter 24 h refluxing under N2 the solvent
  2. customwas 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-92811955578a42c5bdd7fd0220f66114
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Reaction notes

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