Morpholine → HCID 57592528, compound

HRID 1784393Notes

Reaction equation

HRID 1784393 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[C:11](Cl)[N:10]=[C:9](Cl)[N:8]=2)=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[CH:21]([N:24](CC)[CH:25]([CH3:27])C)(C)[CH3:22].CC(N(C)C)=[O:32]>CCOC(C)=O>[Br:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[C:11]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:10]=[C:9]([N:24]3[CH2:25][CH2:27][O:32][CH2:22][CH2:21]3)[N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 57592517908141-98-0

Product 1

HCID 57592528HCID 57592528, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(5-Bromo-furan-2-yl)-2,6-dichloro-pyrimidine (1.93 g, 6.51 mmol) in DMA (35 ml) was added morpholine (2.83 g, 32.54 mmol) and N,N-diisopropylethylamine (4.21 g, 32.54 mmol). The reaction mixture was heated to 70° C. for 7 hours whereupon it was cooled and diluted with EtOAc (100 ml) and then washed with water (2×50 ml), dried (MgSO4), filtered and concentrated in vacuo to give a dark oil. The crude residue was purified by flash chromatography (SiO2) (1:3—EtOAc:Hexanes) to give the title compound as a white crystalline solid (0.95 g, 37%). m/z (LC-MSW, ESP):396 [M+H]+, R/T=4.38 mins.

Workup

  1. temperaturewas cooled
  2. washwashed with water (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a dark oil
  7. customThe crude residue was purified by flash chromatography (SiO2) (1:3—EtOAc:Hexanes)

Sources & evidence

ORD record
ord-dc280072dcda42c8ba814fb64f18c298
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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