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

HRID 1868474Notes

Reaction equation

HRID 1868474 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:9]([CH3:28])=[N:10][C:11]2[N:12]([CH:22]=[C:23]([C:25]([OH:27])=O)[N:24]=2)[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C[N:32]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-].CCN(C(C)C)C(C)C>C1COCC1>[C:25]([C:23]1[N:24]=[C:11]2[N:10]=[C:9]([CH3:28])[C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]2[CH:22]=1)(=[O:27])[NH2:32]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 579824816-(Tert-butoxycarbonyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid

Product 1

HCID 57982465Tert-butyl 2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylateYield 112.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-(tert-butoxycarbonyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (Example 155, Step 1, 500 mg, 1.18 mmol) in THF (10 mL) at room temperature was added PyBOP (787 mg, 1.78 mmol), HOBt (240 mg, 1.18 mmol), NH4Cl (95 mg, 1.78 mmol) and iPr2NEt (0.4 mL, 2.37 mmol). After 24 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with 1N HCl, 1N NaOH and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded tert-butyl 2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (560 mg, 100%) as a light yellow solid.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with 1N HCl, 1N NaOH and brine
  4. dry with materialto drying over anhydrous MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-d5c98865851245fc8a56d815ed6a2e7b
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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