Sodium Hydroxide → HCID 58691599, compound

HRID 856011Notes

Reaction equation

HRID 856011 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[S:19][CH:20]=4)[CH:13]=[N:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CCCCO>[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[S:19][CH:20]=4)[CH:13]=[N:12][C:11]=23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58691611HCID 58691611, compound

Product 1

HCID 58691599HCID 58691599, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of methyl 4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)thiophene-2-carboxylate (5-2, 2.0 g, 6.0 mmol, 1 equiv) in a mixture of aqueous sodium hydroxide solution (1N, 18 mL, 18 mmol, 3.0 equiv) and n-BuOH (100 mL) was heated at reflux for 1 hour. The reaction mixture was concentrated, and the residue was suspended in aqueous 1 N hydrogen chloride solution (100 mL) and filtered. The filtered solid was washed with water and dried to give 4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)thiophene-2-carboxylic acid (5-3). 1H NMR (400 MHz, DMSO-d6) δ 9.68 (d, 1H, J=2.4 Hz), 9.15 (d, 1H, J=2.2 Hz), 8.79 (s, 1H), 8.48 (d, 1H, J=1.6 Hz), 8.41 (d, 1H, J=1.6 Hz), 8.16 (br d, 1H, J=7.8 Hz), 7.46 (br t, 2H, J=7.8 Hz), 7.26 (t, 1H, J=7.5 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. filtrationfiltered
  5. washThe filtered solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-73fdf953098f447388114dad3a98b9f6
Source dataset
uspto-grants-2007_08
Patent number
US07262199B2

Reaction notes

Loading…