4-Nitrophenyl chloroformate → HCID 10671680, compound

HRID 2085383Notes

Reaction equation

HRID 2085383 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:22]2[NH:27][C:26]([O:28][CH3:29])=[N:25][C:24]([CH3:30])=[C:23]2[C:31]([O:33][CH3:34])=[O:32])[CH:18]=[CH:19][C:20]=1[F:21]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:14][C:15]1[CH:16]=[C:17]([CH:22]2[N:27]([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:26]([O:28][CH3:29])=[N:25][C:24]([CH3:30])=[C:23]2[C:31]([O:33][CH3:34])=[O:32])[CH:18]=[CH:19][C:20]=1[F:21]

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 178498444HCID 178498444, compound

Product 1

HCID 10671680HCID 10671680, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl chloroformate (1.82 g, 9.04 mmol) was added to a solution of 6-(3,4-difluorophenyl)-1,6-dihydro-2-methoxy-5-methoxycarbonyl-4-methylpyrimidine (2.82 g, 9.46 mmol) and 4-dimethylaminopyridine (1.16 g, 9.52 mmol) in CH2Cl2 (50 mL), at 0-5° C. and the mixture was then allowed to warm to room temperature. After 12 h, the solvent was evaporated and the residue was purified by flash chromatography (EtOAc/hexane, 1/9 to 3/20), giving the desired product as white crystals (3.72, 85%): mp 172-174° C.

Workup

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

Sources & evidence

ORD record
ord-e978543b9a7d4a59aefae131327cbd75
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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