Methyl chloroformate → HCID 22725146, compound

HRID 1387382Notes

Reaction equation

HRID 1387382 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[CH:15]=[C:14]([CH2:25][CH3:26])[N:13]=[C:12]1[O:27][CH3:28])=[O:10])C1C=CC=CC=1.Cl[C:30]([O:32][CH3:33])=[O:31]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:33]([O:32][C:30]([C:15]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[N:11]([C:9]([O:8][CH3:1])=[O:10])[C:12]([O:27][CH3:28])=[N:13][C:14]=1[CH2:25][CH3:26])=[O:31])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 86757222HCID 86757222, compound

Product 1

HCID 22725146HCID 22725146, compoundYield 135%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of (benzyloxycarbonyl)-1,6-dihydro-2-methoxy-4-ethyl-6-(3,4-diflurophenyl)pyrimidine (0.6 g, 1.5 mmol) and 4-(N,N-dimethylamino)pyridine (0.32 g, 2.66 mmol) in CH2Cl2 (6 mL) was added methyl chloroformate (0.2 mL, 2.66 mmol) at room temperature. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel with 3:1 Petroleum ether/EtOAC as the eluting system to obtain 0.45 g (78% yield) of (−)-5-(benzyloxycarbonyl)-4-ethyl-1,6-dihydro-2-methoxy-6-(3,4-difluorophenyl)-1-[methoxy-carbonyl]pyrimidine as a colorless oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica gel with 3:1 Petroleum ether/EtOAC as the eluting system

Sources & evidence

ORD record
ord-248910c34bd24c12aa2216a3744d82b3
Source dataset
uspto-grants-2001_07
Patent number
US06268369B1

Reaction notes

Loading…