Potassium Carbonate → HCID 86633886, compound

HRID 1687151Notes

Reaction equation

HRID 1687151 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([Cl:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[Cl:17][C:18]1[N:23]=[C:22]([NH:1][C:2]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])[C:21]([Cl:25])=[CH:20][N:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 105609362-Amino-5-(morpholin-4-yl)benzamide

Product 1

HCID 86633886HCID 86633886, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-amino-5-morpholin-4-yl-benzamide (820.0 mg, 3.71 mmol, Heterocyclic Comm. 2001, 7, 473-480), 2,4,5-trichloropyrimidine (679.8 mg, 3.71 mmol) and potassium carbonate (614.6 mg, 4.45 mol) in THF (10 mL) was stirred at 50° C. for 20 h and at RT for 6 days. The reaction was diluted with water (10 mL) and extracted into EtOAc. The organic layer was washed with NaHCO3, brine and dried by passing through a funnel filled with MgSO4. The filtrate was evaporated and the residue triturated with ether (5×3 mL) to afford 2-(2,5-dichloro-pyrimidin-4-ylamino)-5-morpholin-4-yl-benzamide as a yellow solid (0.75 g) that was used without further purification in the subsequent step.

Workup

  1. extractionextracted into EtOAc
  2. washThe organic layer was washed with NaHCO3, brine
  3. customdried
  4. customby passing through a funnel
  5. additionfilled with MgSO4
  6. customThe filtrate was evaporated
  7. customthe residue triturated with ether (5×3 mL)

Sources & evidence

ORD record
ord-68f61333f0904019bf65dc829d3e29f2
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…