Pyridine → HCID 22725169, compound

HRID 2085430Notes

Reaction equation

HRID 2085430 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[F:14][C:15]1[CH:16]=[C:17]([CH:23]2[NH:28][C:27]([O:29][CH3:30])=[N:26][C:25]([CH3:31])=[C:24]2[C:32](=[O:34])[CH3:33])[CH:18]=[C:19]([F:22])[C:20]=1[F:21].N1C=CC=CC=1>C(Cl)Cl>[F:14][C:15]1[CH:16]=[C:17]([CH:23]2[N:28]([C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[C:27]([O:29][CH3:30])=[N:26][C:25]([CH3:31])=[C:24]2[C:32](=[O:34])[CH3:33])[CH:18]=[C:19]([F:22])[C:20]=1[F:21]

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

4-Nitrophenyl chloroformate (1.886 g, 9.38 mmol) was added to a solution of 6-(3,4,5-trifluorophenyl)-1,6-dihydro-2-methoxy-5-acetyl-4-methylpyrimidine (2.80 g, 9.38 mmol) and pyridine (10 mL) in CH2Cl2 (200 mL) at 0-5° C. and then the mixture was allowed to warm to room temperature. After 12 h, the solvent was evaporated and the residue was purified by flash chromatography (CH2Cl2/EtOAc, 9/1 to 20/3), giving the desired product as a white powder (4.0 g, 92%).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by flash chromatography (CH2Cl2/EtOAc, 9/1 to 20/3)

Sources & evidence

ORD record
ord-f71533b4f3bb420797d775ed2239e1e5
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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