3,5-Dimethylaniline → N-(3,5-dimethylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine

HRID 968248Notes

Reaction equation

HRID 968248 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([CH3:30])[CH:29]=1)[NH2:26]>>[CH3:22][C:23]1[CH:24]=[C:25]([NH:26][C:5]2[N:10]=[C:9]([N:11]3[CH:15]=[CH:14][N:13]=[C:12]3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:8]=[CH:7][N:6]=2)[CH:27]=[C:28]([CH3:30])[CH:29]=1

Participants

3

Reactant 2

HCID 79493,5-DimethylanilineHCID 22288411HCID 22288411, compound

Product 1

HCID 5329417N-(3,5-dimethylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine

Conditions

Temperature
100 °C

Procedure

2-(Methylsulfonyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (1-3, 100 mg, 0.33 mmol) and 3,5-dimethylaniline (0.21 ml, 1.66 mmol) were combined neat and heated to 100° C. After 1 hour the mixture was heated to 130° C. After 1 hour, the reaction was partitioned between a pH 5.2 citrate solution and DCM. The aqueous phase was extracted 2× with DCM and the combined organic extracts were dried over Na2SO4, filtered, concentrated and cooled to room temperature. Purification by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA) was followed by purification by flash column chromatography (2% MeOH/CH2Cl2) gave the title compound as a white solid. 1H-NMR (300 MHz, CDCl3) δ 8.27 (d, J=5.5 Hz, 1H), 7.66 (d, J=1.2 Hz, 1H), 7.53 (m, 2H), 7.40 (m, 4H), 7.18 (m, 2H), 7.11 (s, 1H), 6.74 (s, 1H), 6.25 (d, J=5.5 Hz, 1H), 2.32 (s, 6H). mp=183° C.

Workup

  1. temperatureAfter 1 hour the mixture was heated to 130° C
  2. customthe reaction was partitioned between a pH 5.2 citrate solution and DCM
  3. extractionThe aqueous phase was extracted 2× with DCM
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperaturecooled to room temperature
  8. customPurification by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)
  9. customwas followed by purification by flash column chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9e7c4d15eedc46349433f9a69beacd01
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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