Sodium Hydroxide → HCID 17965790, compound

HRID 32585Notes

Reaction equation

HRID 32585 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:15]([CH2:16][CH:17]=O)[CH:14]=[N:13][C:12]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[OH-].[Na+]>CC(O)=O>[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:17][CH2:16][N:15]2[C:11]([C:9]3[S:8][C:4]4[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=4[CH:10]=3)=[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:13]=[CH:14]2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 86601641HCID 86601641, compound2×

Product 1

HCID 17965790HCID 17965790, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]acetaldehyde (Intermediate 74) (100 mg) and N-methyl piperazine (100 μL) were stirred in AcOH (1 mL) for 15 minutes. Na(AcO)3BH (70 mg) was added and the reaction allowed to stir overnight. The reaction was made basic with 2M NaOH (50 mL) and then the product extracted with DCM (3×50 mL). The organics were washed with water (30 mL), brine (30 mL), dried (MgSO4) and concentrated in vacuo. The product was purified by flash chromatography on silica eluting with DCM:7N NH3 in MeOH. (95:5) to afford the title compound as a solid (32 mg, 28%);

Workup

  1. extractionthe product extracted with DCM (3×50 mL)
  2. washThe organics were washed with water (30 mL), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica eluting with DCM

Sources & evidence

ORD record
ord-9fecc8cf3f5c467bafb862ee885e54df
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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