Sodium ethoxide → HCID 178451642, compound

HRID 2406215Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][C:7]1=O)=O)C.[O-]CC.[Na+].Cl.[CH:25]([NH2:27])=[NH:26]>CCO>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]2[C:4]([OH:3])=[N:27][CH:25]=[N:26][C:7]=2[CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

3-Oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (4.6 g, 16.8 mmol) was dissolved in EtOH (90 mL), and sodium ethoxide (2.3 g, 33.6 mmol) and formamidine hydrochloride (2.0 g, 25.2 mmol) were sequentially added. The resulting suspension was heated to 70° C. and stirred for 5 hours, and then the reaction mixture was cooled to room temperature and concentrated. The residue was dissolved in saturated ammonium chloride and extracted with ethyl acetate. The aqueous phase was adjusted to pH ˜5.5 using concentrated AcOH, and extracted several more times with ethyl acetate. The combined organic layers were sequentially washed with water and brine, dried, and concentrated to afford 4-hydroxy-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester as a brown solid (1.8 g, 42% yield). MS (ESI) m/e (M+H+)=251.28

Workup

temperaturethe reaction mixture was cooled to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in saturated ammonium chloride
extractionextracted with ethyl acetate
extractionextracted several more times with ethyl acetate
washThe combined organic layers were sequentially washed with water and brine
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-4d57dc5ab3ca4e52953c84e6bac2be92
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809352B2

Reaction notes

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