1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178436962, compound

HRID 2085419Notes

Reaction equation

HRID 2085419 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[N:14](C(N[C@@H](C3C=CC=CC=3)C)=O)[C:13]([O:26][CH3:27])=[N:12][C:11]([CH2:28][CH3:29])=[C:10]2[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH:5]=[CH:6][C:7]=1[F:8].N12CCCN=C1CCCCC2>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:14][C:13]([O:26][CH3:27])=[N:12][C:11]([CH2:28][CH3:29])=[C:10]2[C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69874997HCID 69874997, compound

Product 1

HCID 178436962HCID 178436962, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a stirred solution of (+)-benzyl 6-(3,4-difluorophenyl)-4-ethyl-2-methoxy-1-({[(1R)-1-phenylethyl]amino}carbonyl)-1,6-dihydro-5-pyrimidinecarboxylate (17.1 mmol, 9.35 g) in CH2Cl2 was added 1,8-diazabicyclo[5,4,0]-undec-7-ene (17.1 mmol, 2.56 mL) and stirring was continued for 16 h at room temperature. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel with 3:1 EtOAc/Hexanes as the eluting system. 5.27 g of the (+)-benzyl 6-(3,4-difluorophenyl)-4-ethyl-2-methoxy-1,6-dihydro-5-pyrimidinecarboxylate was obtained (77% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash column chromatography on silica gel with 3:1 EtOAc/Hexanes as the eluting system

Sources & evidence

ORD record
ord-252a59b5330148eebf6ccd1da59b7956
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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