Piperazine → 6-[1-(3,4Dimethoxybenzyl)-4-phenyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin

HRID 32513Notes

Reaction equation

HRID 32513 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][N:7]=[CH:8][C:9]1[S:17][C:12]2[N:13]=[CH:14][N:15]=[CH:16][C:11]=2[CH:10]=1.N1[CH2:28][CH2:27][NH:26][CH2:25]C1>C1COCC1.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][N:7]1[C:8]([C:9]2[S:17][C:12]3[N:13]=[CH:14][N:15]=[CH:16][C:11]=3[CH:10]=2)=[C:27]([C:28]2[CH:5]=[CH:4][CH:3]=[CH:20][CH:19]=2)[N:26]=[CH:25]1

Participants

6

Reactant 2

HCID 4837PiperazineHCID 17965764N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amine2×

Product 1

HCID 179658266-[1-(3,4Dimethoxybenzyl)-4-phenyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidinYield 96.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3,4Dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amine (intermediate 14) (76 mg), PhTosMIC (99 mg) and piperazine (31 mg) in THF (5 mL) were stirred under an inert atmosphere for 6 days. The reaction mixture was diluted with EtOAc and water. The organic layer was separated and the aqueous layer extracted with EtOAc (2×15 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with hexane:EtOAc (1:4) afforded the title compound as a pale yellow solid (50 mg, 48%);

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with EtOAc (2×15 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica eluting with hexane:EtOAc (1:4)

Sources & evidence

ORD record
ord-4b3e7aa1638b4fe3a08f04a769bfd741
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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