Methyl chloroformate → HCID 22725146, compound

HRID 2086909Notes

Reaction equation

HRID 2086909 reaction equation
N1C=CC=NC=1.[CH2:7]([O:14][C:15]([C:17]1[CH:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)[NH:21][C:20]([O:31][CH3:32])=[N:19][C:18]=1[CH2:33][CH3:34])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:36]([O:38][CH3:39])=[O:37]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:7]([O:14][C:15]([C:17]1[CH:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)[N:21]([C:36]([O:38][CH3:39])=[O:37])[C:20]([O:31][CH3:32])=[N:19][C:18]=1[CH2:33][CH3:34])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 9260PyrimidineHCID 178436962HCID 178436962, compound

Product 1

HCID 22725146HCID 22725146, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(−)-5-(Benzyloxycarbonyl)-4-ethyl-1,6-dihydro-2-methoxy-6-(3,4-difluorophenyl)-1-methoxycarbonyl]pyrimidine. To a well stirred solution of (−)-5-(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-[methoxycarbonyl]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-2a4133d36197439cb2d23c5532f48644
Source dataset
uspto-grants-2004_04
Patent number
US06727257B1

Reaction notes

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