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

HRID 1868483Notes

Reaction equation

HRID 1868483 reaction equation
[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[N:8]2[CH:18]=[C:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:20]=[C:7]2[NH:6][C:5]=1[CH3:26])(=[O:3])[NH2:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1>[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:3])[NH2:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 136057109Methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidin-2-yl)acetate

Product 1

HCID 57982488Methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetateYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidin-2-yl)acetate (1.05 g, 2.66 mmol) in THF (30 mL was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (604 mg, 2.66 mmol). After 30 min, CH2Cl2 (100 mL) and satd aq NaHCO3 (50 mL) were added. The layers were separated, the aqueous layer extracted with an additional 50 mL of CH2Cl2, and the combined CH2Cl2 extracts were washed with satd aq NaHCO3 (3×50 mL). The organic solution was dried with MgSO4, filtered, and concentrated under reduced pressure to yield methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetate (816 mg, 2.08 mmol, 78%) as a pale grey-green solid contaminated with 11% (by HPLC analysis) of the starting material. This material was used without further purification.

Workup

  1. additionwere added
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with an additional 50 mL of CH2Cl2
  4. washthe combined CH2Cl2 extracts were washed with satd aq NaHCO3 (3×50 mL)
  5. dry with materialThe organic solution was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d44c6ddc697d448b99c16f2b33429754
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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