Triethylamine → HCID 136007755, compound

HRID 1022982Notes

Reaction equation

HRID 1022982 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-41d9b9453b7641f0820853e73a7a52a0
Source dataset
uspto-grants-2014_05
Patent number
US08722660B2

Reaction notes

Loading…