Pyridine → HCID 22725169, compound

HRID 565215Notes

Reaction equation

HRID 565215 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[NH:15][C:14]([O:16][CH3:17])=[N:13][C:12]([CH3:18])=[C:11]2[C:19](=[O:21])[CH3:20])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].N1C=CC=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[N:15]([C:29]([O:31][C:32]3[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=3)=[O:30])[C:14]([O:16][CH3:17])=[N:13][C:12]([CH3:18])=[C:11]2[C:19](=[O:21])[CH3:20])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 178494173HCID 178494173, compound

Product 1

HCID 22725169HCID 22725169, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3,4,5-trifluorophenyl)-1,6-dihydro-2-methoxy-5-acetyl-4-methylpyrimidine (2.8 g, 9.38 mmol) and pyridine (10 mL) in CH2Cl2 (200 mL) at 0-5° C. was added 4-nitrophenyl chloroformate (1.886 g, 9.38 mmol) and the mixture was allowed to warm to room temperature. After 12 hours solvent was evaporated and the residue was purified by flash column chromatography (SiO2, dichloromethane/EtOAc, 10%-15%) to obtain the product as a white powder (4.0 g, 92%).

Workup

  1. customAfter 12 hours solvent was evaporated
  2. customthe residue was purified by flash column chromatography (SiO2, dichloromethane/EtOAc, 10%-15%)

Sources & evidence

ORD record
ord-64dcf688aa694df0a1b01a3e66ff231d
Source dataset
uspto-grants-2001_01
Patent number
US06172066B2

Reaction notes

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