Cumylamine → HCID 22346621, compound

HRID 897396Notes

Reaction equation

HRID 897396 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:3]=1.[C:23]([NH2:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:25])[CH3:24]>C(O)(C)C>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:5]2[C:6](=[O:9])[N:7]([CH3:8])[C:2]([NH:32][C:23]([CH3:25])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:24])=[N:3][C:4]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 68509CumylamineHCID 22346644HCID 22346644, compound

Product 1

HCID 22346621HCID 22346621, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Chloro-3-methyl-6-(4-pyridyl)-5-(4-fluorophenyl)-4(3H)-pyrimidinone (5.43 g, 17.2 mmol) and cumyl amine (4.65 g, 34.4 mmol) were combined in dry isopropyl alcohol (ca. 40 mL) and the mixture was heated at reflux for 48 h. The reaction was cooled to RT, the solvent was evaporated in vacuo and the residue was partitioned between sat. aq. NaHCO3 and CHCl3. The organic layer was dried over Na2SO4 and then concentrated. The residue was purified by flash chromatography (1% MeOH/NH3:CHCl3) to provide the product as a tan solid; MS: m/z (M+H)+ 415; C25H23FN4O requir. 414.5.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 48 h
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was partitioned between sat. aq. NaHCO3 and CHCl3
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (1% MeOH/NH3:CHCl3)

Sources & evidence

ORD record
ord-0dbfece524a448f495f9cbe2416cdff3
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

Loading…