Phosgene → rac-(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 1894314Notes

Reaction equation

HRID 1894314 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:34])[C@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[NH:11][C:10]([C:21]3[C:22]([O:31][CH2:32][CH3:33])=[N:23][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[N:25][CH:26]=3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:42](Cl)([Cl:44])=[O:43]>ClCCl.C1(C)C=CC=CC=1>[C:27]([C:24]1[N:23]=[C:22]([O:31][CH2:32][CH3:33])[C:21]([C:10]2[N:11]([C:42]([Cl:44])=[O:43])[C:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([CH3:34])[N:9]=2)=[CH:26][N:25]=1)([CH3:28])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 68938683HCID 68938683, compound

Product 1

HCID 76588520rac-(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2-tert-butyl-4-ethoxy-pyrimidine (850 mg, 1.71 mmol) and triethylamine (600 uL, 4.28 mmol) in 10 mL of dichloromethane at 0° C. was added 1.88 mL solution of 20% phosgene in toluene (Fluka). After stirring for 30 min the mixture was concentrated to dryness under reduced pressure. Purification by flash column chromatography on silica gel, eluting with 10-20% of ethyl acetate in hexane provided 861 mg of rac-(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride as an off-white solid.

Workup

  1. concentrationwas concentrated to dryness under reduced pressure
  2. customPurification by flash column chromatography on silica gel
  3. washeluting with 10-20% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-14f66d6438a042bbb9c2454cf9a4e585
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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