2,6-Di-tert-butyl-4-methylphenol → 6-Butyl-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine-4(3H)-one

HRID 1110053Notes

Reaction equation

HRID 1110053 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15](=O)[CH2:16][CH2:17][CH2:18][CH3:19])[C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.Cl.[C:22]([NH2:25])(=[NH:24])[CH3:23].C([O-])(=O)C.[Na+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>CN(C=O)C.[Cl-].[Na+].O>[CH2:16]([C:15]1[N:24]=[C:22]([CH3:23])[NH:25][C:10](=[O:12])[C:9]=1[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1)[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 67170Acetamidine monohydrochlorideHCID 517045Sodium AcetateHCID 19018799Ethyl 2-[(4-iodophenyl)methyl]-3-oxoheptanoate

Product 1

HCID 1360140486-Butyl-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine-4(3H)-oneYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2.46 g (6.33 mmol) ethyl 2-[(4-iodophenyl)methyl]-3-oxoheptanoate, 6.0 g (63.3 mmol) acetamidine hydrochloride, 5.2 g (63.3 mmol) sodium acetate, and 84 mg (0.381 mmol) 2,6-di-tert-butyl-4-methylphenol in 30 mL DMF was heated to 153° C. for 12 hours. The cooled reaction mixture was poured into brine and extracted 3 times with ether. The combined organic material was washed with brine, dried over MgSO4, stripped of solvent in vacuo, then was medium pressure chromatographed on silica gel using 1/65/34 AcOH/EtOAc/hexane to give 485 mg of the title compound, 20% yield. Unreacted ethyl 2-[(4-iodophenyl)methyl]-3-oxoheptanoate was recycled. Rf 0.25 in 1/65/34 AcOH/EtOAc/hexane, visualized by UV and ninhydrin stain; 1H-NMR (300 MHz, CDCl3): δ 7.56 (m, 2H), 6.98 (m, 2H), 3.83 (s, 2H), 2.54 (3 line m, 2H), 2.38 (s, 3H), 1.52 (m, 2H), 1.43 (m, 2H), 0.89 (3 line m, 3H).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted 3 times with ether
  3. washThe combined organic material was washed with brine
  4. dry with materialdried over MgSO4
  5. customchromatographed on silica gel using 1/65/34 AcOH/EtOAc/hexane

Sources & evidence

ORD record
ord-c97c102d53e24eb5a80f80745b9a8d02
Source dataset
uspto-grants-1994_06
Patent number
US05324729

Reaction notes

Loading…