Dimethylamine → (5-Chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-pyridin-3-ylmethyl)-dimethyl-amine

HRID 1444105Notes

Reaction equation

HRID 1444105 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:33]OS(C)(=O)=O)[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:17]=[C:16]([N:27]3[CH2:31][CH2:30][CH2:29][CH:28]3[CH3:32])[N:15]=2)[CH2:10][CH2:9]1.[CH3:39][NH:40][CH3:41]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:33][N:40]([CH3:41])[CH3:39])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:17]=[C:16]([N:27]3[CH2:31][CH2:30][CH2:29][CH:28]3[CH3:32])[N:15]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 59168343Methanesulfonic acid 5-chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-pyridin-3-ylmethyl ester

Product 1

HCID 59168230(5-Chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-pyridin-3-ylmethyl)-dimethyl-amine

Procedure

Heat a mixture of methanesulfonic acid 5-chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-pyridin-3-ylmethyl ester with an excess of dimethylamine (1M in THF) in a sealed tube at 80° C. for 2 h. Concentrate under reduced pressure then partition between EtOAc and 10% NaOH solution. Dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify the resulting residue using flash chromatography (10:90:1/MeOH:DCM:NH4OH eluent) to give the title compound.

Workup

  1. temperatureHeat
  2. concentrationConcentrate under reduced pressure
  3. customthen partition between EtOAc and 10% NaOH solution
  4. dry with materialDry the organic layer (Na2SO4)
  5. concentrationconcentrate under reduced pressure
  6. customPurify the resulting residue

Sources & evidence

ORD record
ord-e083bf8709374340907fd4d0cb3d2e75
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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