Diisopropylethylamine → HCID 58504547, compound

HRID 2367557Notes

Reaction equation

HRID 2367557 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[CH2:11]([C@H:13]1[NH:18][CH2:17][C@@H:16]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:20])[O:15][CH2:14]1)[CH3:12].CCN(C(C)C)C(C)C>CC#N.O>[Cl:8][C:6]1[N:5]=[C:4]([NH:9][CH3:10])[N:3]=[C:2]([N:18]2[C@H:13]([CH2:11][CH3:12])[CH2:14][O:15][C@H:16]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[CH2:17]2)[CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 51353731HCID 51353731, compound

Product 1

HCID 58504547HCID 58504547, compoundYield 129.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4,6-Dichloro-N-methyl-2-pyrimidinamine (0.150 g, 0.845 mmol) was added to a 20 mL microwave vial followed by the addition of (2S,5R)-5-ethyl-N-phenyl-2-morpholinecarboxamide (0.198 g, 0.845 mmol) in CH3CN (5 mL) and Hunig's base (0.738 mL, 4.23 mmol). The reaction was irradiated at 150° C. for 10 minutes. The reaction was left in the 20 mL sealed microwave vessel and heated to 100° C. over the weekend. The reaction mixture was diluted with water and extracted with EtOAc (2×). The organic layers were combined and dried to afford the crude title compound (0.410 g). LC-MS (ES) m/z=376 [M+H]+.

Workup

  1. customThe reaction was irradiated at 150° C. for 10 minutes
  2. waitThe reaction was left in the 20 mL
  3. customsealed microwave vessel
  4. extractionextracted with EtOAc (2×)
  5. customdried

Sources & evidence

ORD record
ord-ddc943e4e0604af9a4e98a9340b4e898
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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