N-Aminomorpholine → 2,10-dihydro-10-(4-morpholinyl)imidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-one

HRID 2350858Notes

Reaction equation

HRID 2350858 reaction equation
Cl[C:2]1[C:7]([C:8]([N:10]2[CH2:14][CH2:13][N:12]=[C:11]2SC)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>>[N:18]1([N:17]2[C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=[O:9])[N:10]3[CH2:14][CH2:13][N:12]=[C:11]23)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 20315N-AminomorpholineHCID 143871351-(2-Chloropyridine-3-carbonyl)-2-methylthio-2-imidazoline

Product 1

HCID 143871362,10-dihydro-10-(4-morpholinyl)imidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-oneYield 52%

Conditions

Temperature
160 °C

Procedure

A mixture of 5.00 g (19.5 mmoles) of the product of Example 12 and 6.40 g (62.6 mmoles) of N-aminomorpholine was heated in an oil bath at 160° C. for 1 hour. The resulting mixture was cooled and partitioned between methylene chloride and water. The organic layer was dried (sodium sulfate) and concentrated. The crystalline residue was triturated with hexane. The resulting solid was collected to give 2.75 g of 2,10-dihydro-10-(4-morpholinyl)imidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-one. Melting point 225°-226° C. Total yield 52%. This compound exhibits the following formula: ##STR9##

Workup

  1. temperatureThe resulting mixture was cooled
  2. custompartitioned between methylene chloride and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe crystalline residue was triturated with hexane
  6. customThe resulting solid was collected

Sources & evidence

ORD record
ord-d043a53d9458470d8252831e938c34db
Source dataset
uspto-grants-1989_10
Patent number
US04871732

Reaction notes

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