Triethylamine → Tert-butyl 2-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate

HRID 1868476Notes

Reaction equation

HRID 1868476 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:8]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[N:7]2[CH:28]=1)(=O)[NH2:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.CCN(CC)CC>C(Cl)Cl>[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:8]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[N:7]2[CH:28]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 57982465Tert-butyl 2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate

Product 1

HCID 67021510Tert-butyl 2-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylateYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (Example 156, Step 1, 50 mg, 0.12 mmol) in CH2Cl2 (3 mL) was added TFAA (50 mg, 0.24 mmol) and Et3N (33 μL, 0.24 mmol). After 2 h, the reaction was extracted with H2O and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure afforded tert-butyl 2-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (50 mg, 95% pure) as a yellow oil.

Workup

  1. extractionthe reaction was extracted with H2O and brine
  2. dry with materialto drying over anhydrous MgSO4
  3. filtrationFiltration, concentration under reduced pressure

Sources & evidence

ORD record
ord-b1d2f091c6ff47ed80a51cb51620acd3
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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