4-Nitrophenyl chloroformate → HCID 22725139, compound

HRID 1976583Notes

Reaction equation

HRID 1976583 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[NH:9][C:8]([O:19][CH3:20])=[N:7][C:6]=1[CH2:21][O:22][CH3:23])=[O:4].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[N:9]([C:25]([O:27][C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=2)=[O:26])[C:8]([O:19][CH3:20])=[N:7][C:6]=1[CH2:21][O:22][CH3:23])=[O:4]

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 178494563HCID 178494563, compound

Product 1

HCID 22725139HCID 22725139, compoundYield 246.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of 5-methoxycarbonyl-1,6-dihydro-2-methoxy-4-methoxymethyl-6-(3,4-difluorophenyl)pyrimidine (4.3 g, 3.18 mmol) and 4-(N,N-dimethylamino)pyridine (2.09 g, 17.13 mmol) in CH2Cl2 (100 mL) was added solid 4-nitrophenyl chloroformate (3.45 g, 17.13 mmol) at 0° C. The reaction mixture was stirred for 12 h at room temperature and the solid formed was removed by filtration. Solvent was evaporated from the filtrate and the residue was purified by column chromatography (SiO2, dichloromethane/hexane, 20%-50%) to yield the product as a viscous oil (3.85 g, 59%).

Workup

  1. customthe solid formed
  2. customwas removed by filtration
  3. customSolvent was evaporated from the filtrate
  4. customthe residue was purified by column chromatography (SiO2, dichloromethane/hexane, 20%-50%)

Sources & evidence

ORD record
ord-7c2d8dfef6a54598bcc1491b0fffc254
Source dataset
uspto-grants-2001_05
Patent number
US06228861B1

Reaction notes

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