Barium manganate → 5-[5-(1H-imidazol-2-yl)-2-isopropyl-4-methoxy-phenoxy]-pyrimidine-2,4-diamine

HRID 38357Notes

Reaction equation

HRID 38357 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[C:7]([O:24][CH3:25])=[CH:8][C:9]([CH:21]([CH3:23])[CH3:22])=[C:10]([CH:20]=1)[O:11][C:12]1[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[N:16][CH:17]=1.[Mn]([O-])([O-])(=O)=O.[Ba+2]>C(Cl)Cl>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[C:6]1[C:7]([O:24][CH3:25])=[CH:8][C:9]([CH:21]([CH3:23])[CH3:22])=[C:10]([CH:20]=1)[O:11][C:12]1[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 3084030Barium manganate2×HCID 445736965-[5-(4,5-dihydro-1H-imidazol-2-yl)-2-isopropyl-4-methoxy-phenoxy]-pyrimidine-2,4-diamine

Product 1

HCID 445736955-[5-(1H-imidazol-2-yl)-2-isopropyl-4-methoxy-phenoxy]-pyrimidine-2,4-diamineYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[5-(4,5-dihydro-1H-imidazol-2-yl)-2-isopropyl-4-methoxy-phenoxy]-pyrimidine-2,4-diamine (0.033 g, 0.096 mmol) in dry methylene chloride (25 ml) was added barium manganate (0.4 g, 1.56 mmol). The reaction mixture refluxed over night, after which more of barium manganate (0.1 g) was added, and the mixture was refluxed for another 6 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified with preparative TLC (8% methanol in methylene chloride/0.1% concentrated ammonium hydroxide) to yield 5-[5-(1H-imidazol-2-yl)-2-isopropyl-4-methoxy-phenoxy]-pyrimidine-2,4-diamine as pale yellow solid (0.026 g, 41%).

Workup

  1. temperatureThe reaction mixture refluxed over night
  2. temperaturethe mixture was refluxed for another 6 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified with preparative TLC (8% methanol in methylene chloride/0.1% concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-74dfed4c84a3405bb32d3c2418f20a2a
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

Loading…