2,4-Dichloropyrimidine → HCID 58504837, compound

HRID 2367554Notes

Reaction equation

HRID 2367554 reaction equation
[CH2:1]([C@H:3]1[NH:8][CH2:7][C@@H:6]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[O:5][CH2:4]1)[CH3:2].Cl[C:19]1[N:24]=[CH:23][CH:22]=[C:21]([Cl:25])[N:20]=1.CC[N:28](C(C)C)C(C)C>CC#N.O>[NH2:28][C:19]1[N:24]=[C:23]([N:8]2[C@H:3]([CH2:1][CH3:2])[CH2:4][O:5][C@H:6]([C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:10])[CH2:7]2)[CH:22]=[C:21]([Cl:25])[N:20]=1

Participants

6

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 51353731HCID 51353731, compound

Product 1

HCID 58504837HCID 58504837, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(2S,5R)-5-Ethyl-N-phenyl-2-morpholinecarboxamide (0.3118 g, 1.331 mmol) and 2,6-dichloropyrimidine (0.218 g, 1.331 mmol) were added to a 20 mL microwave vessel and dissolved in CH3CN (5 mL). Hunig's base (1.162 mL, 6.65 mmol) was added, and the reaction was capped and irradiated at 150° C. for 2 hours. The reaction mixture was then diluted with H2O and extracted with EtOAc. The organic layers were combined and dried to afford the title compound (0.419 g). LC-MS (ES) m/z=362 [M+H]+.

Workup

  1. customthe reaction was capped
  2. customirradiated at 150° C. for 2 hours
  3. extractionextracted with EtOAc
  4. customdried

Sources & evidence

ORD record
ord-fab98eabf12741c0b55b0f1492705b0e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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