2-Chloro-6,7-dihydro-4-(4-morpholinyl)-5H-cyclopentapyrimidine → HCID 59362919, compound

HRID 1668827Notes

Reaction equation

HRID 1668827 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]2[CH2:14][CH2:15][CH2:16][C:4]=2[N:3]=1.[CH3:17][O:18][C:19]([C:21]1([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22]1)=[O:20]>C(O)(C)C>[CH3:17][O:18][C:19]([C:21]1([C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:2]3[N:7]=[C:6]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)[C:5]4[CH2:14][CH2:15][CH2:16][C:4]=4[N:3]=3)=[CH:29][CH:30]=2)[CH2:22][CH2:23][CH2:24]1)=[O:20]

Participants

4

Reactant 2

HCID 126028662-Chloro-6,7-dihydro-4-(4-morpholinyl)-5H-cyclopentapyrimidineHCID 593622601215017-84-7

Product 1

HCID 59362919HCID 59362919, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-chloro-4-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidine (0.53 g, 2.8 mmol) and 1-(4-amino-phenyl)-cyclobutanecarboxylic acid methyl ester (0.57 g, 2.8 mmol) in anhydrous isopropanol (10 mL) was stirred under reflux for 18 hours. After cooling to a temperature in the range of 25° C. to 40° C., the mixture was concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel) to afford the title compound as a white solid (0.24 g, 27% yield).

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling to a temperature in the range of 25° C. to 40° C.
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe crude residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-1effcc9c99d149ccbda9a8b9c841f9a9
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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