4-Nitrophenyl chloroformate → HCID 22725157, compound

HRID 1387379Notes

Reaction equation

HRID 1387379 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[NH:12][C:11]([O:22][CH3:23])=[N:10][C:9]=1[CH2:24][O:25][CH3:26])=[O:7])#[N:2].Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:29]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[N:12]([C:28]([O:30][C:31]2[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=2)=[O:29])[C:11]([O:22][CH3:23])=[N:10][C:9]=1[CH2:24][O:25][CH3:26])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 178494564HCID 178494564, compound

Product 1

HCID 22725157HCID 22725157, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of (+)-5-(2-cyanoethoxycarbonyl)-1,6-dihydro-2-methoxy-4-methoxymethyl-6-(3,4-difluorophenyl)pyrimidine (0.82 g, 2.24 mmol) and 4-(N,N-dimethylamino)pyridine (0.329 g, 2.69 mmol) in CH2Cl2 (200 mL) was added a powder of 4-nitrophenyl chloroformate (0.543 g, 2.69 mmol) at room temperature. The solvent was evaporated and the residue was purified by column chromatography on silica gel using dichloromethane/hexane (20%-50%) as the eluent to give (+)-5-(2-cyanoethoxycarbonyl)-4-methoxymethyl-1,6-dihydro-2-methoxy-6-(3,4-difluorophenyl)-1-[(4-nitrophenyloxy)carbonyl] pyrimidine (0.80 g, 67%) as a viscous oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6fc03307e593446ea57d2dbd99c5b28d
Source dataset
uspto-grants-2001_07
Patent number
US06268369B1

Reaction notes

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