Triethylamine → Ethyl 6-(chloromethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate

HRID 1868459Notes

Reaction equation

HRID 1868459 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:13]2[N:12]=[C:11]([CH3:23])[C:10]=1[CH2:24]O.CS([Cl:30])(=O)=O.CCN(CC)CC>C(Cl)Cl>[Cl:30][CH2:24][C:10]1[C:11]([CH3:23])=[N:12][C:13]2[N:14]([CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)[C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46901745Ethyl 5-(2,4-dichlorophenyl)-6-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 46901746Ethyl 6-(chloromethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylateYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 5-(2,4-dichlorophenyl)-6-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (430 mg, 1.12 mmol) in CH2Cl2 (10 mL) was added MsCl (0.1 mL, 1.35 mmol) and Et3N (0.24 mL, 1.69 mmol). After 10 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The mixture was extracted with H2O and brine before drying over MgSO4. Filtration and concentration under reduced pressure gave ethyl 6-(chloromethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (448 mg, 100% crude yield) as a yellow oil.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. extractionThe mixture was extracted with H2O and brine
  4. dry with materialbefore drying over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-dd4fc6afb4cc49958b311a34f1b61ba0
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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