Pyridine → HCID 22725169, compound

HRID 1387381Notes

Reaction equation

HRID 1387381 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., 4-nitrophenyl chloroformate (1.886 g, 9.38 mmol) was added 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-99bb55daaf074aa4ae6f47d33f42978f
Source dataset
uspto-grants-2001_07
Patent number
US06268369B1

Reaction notes

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