Triethylamine → Methyl 2-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetate

HRID 1868484Notes

Reaction equation

HRID 1868484 reaction equation
[C:1]([C:4]1[C:5]([CH3:26])=[N:6][C:7]2[N:8]([CH:18]=[C:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:20]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])(=O)[NH2:2].CCN(CC)CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH4+].[Cl-]>C(Cl)Cl>[C:1]([C:4]1[C:5]([CH3:26])=[N:6][C:7]2[N:8]([CH:18]=[C:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:20]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 25517Ammonium ChlorideHCID 57982488Methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetate

Product 1

HCID 57982479Methyl 2-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetate (766 mg, 1.95 mmol) in CH2Cl2 (20 mL) was added Et3N (592 mg, 5.85 mmol) and trifluoroacetic anhydride (819 mg, 3.90 mmol). The reaction mixture became a dark brown-green solution within 2 min. Satd aq NH4Cl (20 mL) was added after 30 min. The organic layer was washed with 20 mL each of satd aq NaHCO3 and water, followed by drying with MgSO4, filtration, and concentration under reduced pressure. The residue was purified by silica gel chromatography eluting product through a 40 mm i.d. by 150 mm column with 1.5% MeOH in CH2Cl2. Concentration of the fractions containing product gave methyl 2-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetate (583 mg, 80%) as a yellow foam.

Workup

  1. customwithin 2 min
  2. washThe organic layer was washed with 20 mL each of satd aq NaHCO3 and water
  3. dry with materialby drying with MgSO4, filtration, and concentration under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting product through a 40 mm i.d
  6. additionConcentration of the fractions containing product

Sources & evidence

ORD record
ord-5bdc80f7e0aa423cbf7b510b55469bd0
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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