Triethylamine → HCID 136007755, compound

HRID 1409087Notes

Reaction equation

HRID 1409087 reaction equation
Cl.Cl.[CH3:3][C:4]1[NH:8][N:7]=[CH:6][C:5]=1[C:9]1[S:17][C:16]2[C:15](=[O:18])[NH:14][C:13]([C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][NH:20]3)=[N:12][C:11]=2[CH:10]=1.C(N(CC)CC)C>CO>[CH3:3][C:4]1[NH:8][N:7]=[CH:6][C:5]=1[C:9]1[S:17][C:16]2[C:15](=[O:18])[NH:14][C:13]([C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][NH:20]3)=[N:12][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 136333957HCID 136333957, compound

Product 1

HCID 136007755HCID 136007755, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(5-Methyl-1H-pyrazol-4-yl)-2-[(2S)-piperidin-2-yl]thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride (255 mg) produced in Example 83, step D, was suspended in methanol (7 mL), and triethylamine (0.28 mL) was added to give a solution. To the mixture was added basic silica gel (5 g), and they were mixed. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (methanol/ethyl acetate). The object fraction was concentrated under reduced pressure, and ethyl acetate (10 mL) was added the obtained residue. The precipitate was collected by filtration to give the title compound (183 mg) as a white solid.

Workup

  1. customto give a solution
  2. additionTo the mixture was added basic silica gel (5 g), and they
  3. additionwere mixed
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (methanol/ethyl acetate)
  6. concentrationThe object fraction was concentrated under reduced pressure, and ethyl acetate (10 mL)
  7. additionwas added the obtained residue
  8. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4073d885197f4737b4933c243a3b8a37
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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