Iodine → HCID 68752347, compound

HRID 1894324Notes

Reaction equation

HRID 1894324 reaction equation
II.C(=O)([O-])[O-].[K+].[K+].[CH3:9][O:10][C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([CH:19]=O)=[CH:13][N:12]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([NH2:40])([C:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)([NH2:32])[CH3:31])[CH3:29])=[CH:24][CH:23]=1>C(O)(C)(C)C.C(OCC)C>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C@@:28]2([CH3:29])[C@:30]([C:33]3[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=3)([CH3:31])[NH:32][C:19]([C:14]3[C:15]([O:17][CH3:18])=[N:16][C:11]([O:10][CH3:9])=[N:12][CH:13]=3)=[N:40]2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 807IodineHCID 11430Potassium CarbonateHCID 5977822,4-Dimethoxypyrimidine-5-carbaldehydeHCID 15153976HCID 15153976, compound

Product 1

HCID 68752347HCID 68752347, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

The title compound was prepared using the procedure described by Ishihara, M. and Togo, H. Synlett 2006, 2, 227-230 and ibid Tetrahedron 2007, 63,1474-1480. Iodine (172 mg, 0.68 mg) was dissolved in tert-butanol (20 mL) and potassium carbonate (300 mg, 2.2 mmol) was added. 2,4-Dimethoxy-5-formylpyrimidine (100 mg, 0.6 mmol, Frontier) and (rac)-2,3-Bis(4-chloro-phenyl)-butane-2,3-diamine (200 mg, 0.65 mmol) was added to the mixture. This was warmed to 65° C. for 2 h. This was cooled, diluted with ethyl ether (50 mL) and filtered through Celite. After evaporating to dryness, the residue was purified by flash column chromatography (silica gel, eluting with 2-5% methanol/methylene chloride) to give rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2,4-dimethoxy-pyrimidine.

Workup

  1. customThe title compound was prepared
  2. temperatureThis was cooled
  3. filtrationfiltered through Celite
  4. customAfter evaporating to dryness
  5. customthe residue was purified by flash column chromatography (silica gel, eluting with 2-5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-9fe07144d9e9427d9731cb05649f336b
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

Loading…