Diisopropylethylamine → HCID 58504661, compound

HRID 2367558Notes

Reaction equation

HRID 2367558 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[CH:11]1([NH:17][C:18]([C@H:20]2[O:25][CH2:24][C@@H:23]([CH2:26][CH3:27])[NH:22][CH2:21]2)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.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:22]2[C@H:23]([CH2:26][CH3:27])[CH2:24][O:25][C@H:20]([C:18]([NH:17][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[O:19])[CH2:21]2)[CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 51353732HCID 51353732, compound

Product 1

HCID 58504661HCID 58504661, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4,6-Dichloro-N-methyl-2-pyrimidinamine (0.141 g, 0.791 mmol) was added to a 20 mL microwave vial followed by the addition of (2S,5R)—N-cyclohexyl-5-ethyl-2-morpholinecarboxamide (0.190 g, 0.791 mmol) in CH3CN (5 mL) and Hunig's base (0.690 mL, 3.95 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 title compound (0.302 g). LC-MS (ES) m/z=382 [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-e8077720b56e4aa2ba162275eae2a6e5
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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