Sodium Hydroxide → HCID 58999581, compound

HRID 1593590Notes

Reaction equation

HRID 1593590 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([C:18]([O:20]C)=[O:19])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([C:18]([OH:20])=[O:19])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58999591HCID 58999591, compound

Product 1

HCID 58999581HCID 58999581, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

Methyl 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-4-carboxylate (0.2 g, 0.705 mmol) was dissolved in MeOH (10 mL). 10% NaOH solution (1.5 mL) was added. The solution was heated at 85° C. for 1 h. Solvent was removed under reduced pressure. The aqueous. layer was acidified to ca. pH 4. The aqueous layer was then extracted with DCM (2×50 mL) to remove organic impurities. The acidic aqueous layer was dried on the lyophilizer. The resulting solids were washed with MEOH (10 mL) and filtrate concentrated to give 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-4-carboxylic acid (0.173 g, 0.642 mmol, 91%) as a brown oil. The resulting product was used without further purification.

Workup

  1. customSolvent was removed under reduced pressure
  2. extractionThe aqueous layer was then extracted with DCM (2×50 mL)
  3. customto remove organic impurities
  4. customThe acidic aqueous layer was dried on the lyophilizer
  5. washThe resulting solids were washed with MEOH (10 mL) and filtrate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d14ef9f155b348a88b822fa2ade55e33
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

Loading…