Hydrochloric Acid → N-[5-(1,6-Dihydro-4-hydroxy-6-oxo-2-pyrimidinyl)-2-pyridinyl]-2,2-dimethylpropanamide

HRID 1920823Notes

Reaction equation

HRID 1920823 reaction equation
C[O-].[Na+].[C:4]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[N:11][CH:12]=1)(=[NH:6])[NH2:5].C[C:21](C)([C:25]([O-])=[O:26])[C:22]([O-])=[O:23].Cl>CO.O>[OH:26][C:25]1[N:6]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])=[N:11][CH:12]=2)[NH:5][C:22](=[O:23])[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6946994DimethylmalonatHCID 10942334Sodium MethoxideHCID 59198402HCID 59198402, compound

Product 1

HCID 59198397N-[5-(1,6-Dihydro-4-hydroxy-6-oxo-2-pyrimidinyl)-2-pyridinyl]-2,2-dimethylpropanamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
82 °C

Procedure

A suspension of sodium methoxide (432 mg, 8.0 mmol), N-(5-carbamimidoylpyridin-2-yl)pivalamide (880 mg, 4.0 mmol) and dimethylmalonate (457 μL, 4.0 mmol) in 15 mL methanol is refluxed at 82° C. for 14 hours. The resulting suspension is dissolved in 15 mL water and acidified using 6M HCl. The precipitate is filtered, rinsed with water, air/vacuum dried and used in the next step without further purification.

Workup

  1. filtrationThe precipitate is filtered
  2. washrinsed with water, air/vacuum
  3. customdried
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-c8d47ea0ce384935902ec75606d14570
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

Loading…