Water → HCID 86633450, compound

HRID 1668657Notes

Reaction equation

HRID 1668657 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][CH2:25][NH2:26])=[CH:16]1.CCN(C(C)C)C(C)C.O>CC(O)C>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=[C:2]([NH:26][CH2:25][CH2:24][C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:15][CH:16]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1150TryptamineHCID 81531DiisopropylethylamineHCID 120574654,6-dichloro-2-(2-pyridinyl)pyrimidine2×

Product 1

HCID 86633450HCID 86633450, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4,6-Dichloro-2-pyridin-2-yl-pyrimidine (Intermediate F) (1 eq, 8.85 mmol, 2.0 g) and 2-(1H-indol-3-yl)-ethylamine (1 eq, 8.85 mmol, 1.42 g) are dissolved in iPrOH (10 ml). DIPEA (2 eq, 17.7 mmol, 2.29 g) is added and the resulting mixture is heated using microwave radiation at 130° C. for 20 min. The reaction mixture is added to water and extracted with EtOAc. The combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude residue is crystallised from EtOAc giving the title compound [M+H]+=350.

Workup

  1. temperaturethe resulting mixture is heated
  2. customat 130° C.
  3. customfor 20 min
  4. extractionextracted with EtOAc
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue is crystallised from EtOAc giving the title compound [M+H]+=350

Sources & evidence

ORD record
ord-31020f863ec64a8aa41a32598dba3fda
Source dataset
uspto-grants-2011_08
Patent number
US07989458B2

Reaction notes

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