Diisopropylethylamine → 4-(3-Chloro-4-fluoro-phenyl)-6-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine

HRID 1444114Notes

Reaction equation

HRID 1444114 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[C:4]([N:16]2[CH2:20][CH2:19][CH2:18][CH:17]2[CH3:21])[N:3]=1.[CH3:22][C:23]1[C:24]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[N:25][CH:26]=[C:27]([N+:29]([O-:31])=[O:30])[CH:28]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([N:35]3[CH2:36][CH2:37][N:32]([C:24]4[C:23]([CH3:22])=[CH:28][C:27]([N+:29]([O-:31])=[O:30])=[CH:26][N:25]=4)[CH2:33][CH2:34]3)[N:3]=[C:4]([N:16]3[CH2:20][CH2:19][CH2:18][CH:17]3[CH3:21])[N:5]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 566870601-(3-Methyl-5-nitropyridin-2-yl)piperazineHCID 866495774-Chloro-6-(3-chloro-4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine

Product 1

HCID 114971584-(3-Chloro-4-fluoro-phenyl)-6-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a mixture of 4-chloro-6-(3-chloro-4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl) -pyrimidine (210 mg), 1-(3-Methyl-5-nitro-pyridin-2-yl)-piperazine, and DIEA (185 mg, 1.44 mmol) in DMA at 120°C. for 16 h. Concentrate under reduced pressure and partition between EtOAc and brine. Dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify the residue by flash column eluting with EtOAc-Hexanes (1:4) to afford the title compound as a yellow solid.

Workup

  1. temperatureHeat
  2. concentrationConcentrate under reduced pressure
  3. custompartition between EtOAc and brine
  4. dry with materialDry the organic layer (Na2SO4)
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash column
  7. washeluting with EtOAc-Hexanes (1:4)

Sources & evidence

ORD record
ord-191dd0a7ff574587950f7530b7a8752d
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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