Pyridine → HCID 21998647, compound

HRID 1976592Notes

Reaction equation

HRID 1976592 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[NH:15][C:14]([O:25][CH3:26])=[N:13][C:12]=1[CH2:27][O:28][CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:37]([O:39][C:40]1[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=1)=[O:38]>C(Cl)Cl>[CH2:1]([O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[N:15]([C:37]([O:39][C:40]2[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=2)=[O:38])[C:14]([O:25][CH3:26])=[N:13][C:12]=1[CH2:27][O:28][CH3:29])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 178494560HCID 178494560, compound

Product 1

HCID 21998647HCID 21998647, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of (+)-5-benzyloxycarbonyl-1,6-dihydro-2-methoxy-4-methoxymethyl-6-(3,4-difluorophenyl)pyrimidine (1.25 g, 3.0 mmol) and pyridine (2 mL) in CH2Cl2 (20 mL) was added powdered 4-nitrophenyl chloroformate (1 g, 5 mmol) at room temperature. Solvent was evaporated and the residue was purified by column chromatography on silica gel using CHCl3/EtOAc (20%-50%) as the eluent to give (+)-5-benzyloxycarbonyl-4-methoxymethyl-1,6-dihydro-2-methoxy-6-(3,4-difluorophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine (1.70 g, 86%) as a viscous oil. [α]D=+200 (c=1.215 g in 100 mL CHCl3) g) (+)-6-(3,4-Difluorophenyl)-1-{N-[2-(4-cyano-4-phenylcyclohex-1-ylamino)-ethyl]}carboxamido-5-benzyloxycarbonyl-4-methoxymethyl-2-oxo 1,2,3,6-tetrahydropyrimidine (cis isomer).

Workup

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

Sources & evidence

ORD record
ord-83dd873df5644dea809de015b02a93e9
Source dataset
uspto-grants-2001_05
Patent number
US06228861B1

Reaction notes

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