Morpholine → 2-Chloro-6,7-dihydro-4-(4-morpholinyl)-5H-cyclopentapyrimidine

HRID 1668826Notes

Reaction equation

HRID 1668826 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:13]=[C:12](Cl)[C:11]2[CH2:15][CH2:16][CH2:17][C:10]=2[N:9]=1>C(O)C>[Cl:7][C:8]1[N:13]=[C:12]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[C:11]2[CH2:15][CH2:16][CH2:17][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidine

Product 1

HCID 126028662-Chloro-6,7-dihydro-4-(4-morpholinyl)-5H-cyclopentapyrimidineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Morpholine (0.32 mL, 3.7 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.5 g, 2.65 mmol) in anhydrous ethanol (5 mL) and stirred at a temperature in the range of 65° C. to 85° C. for 10 to 16 hours. Thereafter, the mixture was concentrated under reduced pressure and the crude was diluted with anhydrous ether. After standing at a temperature in the range of 5° C. to 10° C. for 2 hours, the precipitated solid was filtered and washed with ether. The solid was recrystallized from ethyl acetate to afford the title compound as a pale yellow solid (0.54 g, 86% yield).

Workup

  1. concentrationThereafter, the mixture was concentrated under reduced pressure
  2. additionthe crude was diluted with anhydrous ether
  3. waitAfter standing at a temperature in the range of 5° C. to 10° C. for 2 hours
  4. filtrationthe precipitated solid was filtered
  5. washwashed with ether
  6. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-955a15a83ddd434ea18ce6186a460306
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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