2-Methoxyethanol → [4-(2,4-Dimethyl-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine

HRID 855608Notes

Reaction equation

HRID 855608 reaction equation
[N+]([O-])(O)=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[NH:14])=[CH:8][CH:7]=1.[OH-].[Na+].CO[CH2:20][CH2:21]O>>[CH3:10][C:9]1[NH:12][CH:13]=[C:20]([CH3:21])[C:8]=1[C:7]1[CH:6]=[CH:11][N:15]=[C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([F:5])=[CH:11][CH:10]=2)[N:14]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 1785125564-Fluorophenylguanidine nitrate

Product 1

HCID 9856973[4-(2,4-Dimethyl-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amineYield 62%

Procedure

To a mixture of 3-dimethylamino-1-(2,4-dimethyl-1H-pyrrol-3-yl)-propenone (1 mmol, 0.19 g) and 4-fluorophenyl guanidine nitrate (2 mmol, 0.44 g) in 2-methoxyethanol (5 mL) was added NaOH (40 mg). The reaction mixture was heated at 100–120° C. under N2 for 6 h. The solvent was evaporated to dryness and the residue was purified by flash chromatography (1:2 EtOAc/PE). Recrystallisation from EtOAc/PE afforded the title compound (174 mg, 62%) as brown crystals. 1H-NMR (CDCl3) δ: 2.21 (s, 3H, CH3), 2.43 (s, 3H, CH3), 6.33 (s, 1H, pyrrolyl-H), 6.73 (d, 1H, J=5.3 Hz, pyrimidinyl-H), 7.00 (m, 2H, Ph-H), 7.79 (m, 2H, Ph-H), 8.28 (d, 1H, J=5.3 Hz, pyrimidinyl-H), 9.16 (s, 1H, NH), 10.59 (s, 1H, NH).

Workup

  1. temperatureThe reaction mixture was heated at 100–120° C. under N2 for 6 h
  2. customThe solvent was evaporated to dryness
  3. customthe residue was purified by flash chromatography (1:2 EtOAc/PE)
  4. customRecrystallisation from EtOAc/PE

Sources & evidence

ORD record
ord-13dfefb17e6c4928b8a859956e34b5f2
Source dataset
uspto-grants-2007_08
Patent number
US07262202B2

Reaction notes

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