Pyridine → HCID 136038011, compound

HRID 1498756Notes

Reaction equation

HRID 1498756 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].N1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1.CCOC(C)=O>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:16]([C:17]1[CH:2]=[C:3]([CH3:4])[C:7]([O:13][CH3:14])=[C:19]([CH3:20])[CH:18]=1)=[N:1]2

Participants

5

Reactant 2

HCID 1049PyridineHCID 203490162-Amino-4,6-dimethoxybenzamide

Product 1

HCID 136038011HCID 136038011, compoundYield 158.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-amino-4,6-dimethoxybenzamide (0.0990 g, 0.555 mmol) and pyridine (44.9 μL, 0.555 mmol) in THF (2.02 mL) was added dropwise a solution of the acid chloride (crude residue described above) in THF (925 μL). After 16 h, the mixture was diluted with EtOAc (300 mL), washed with saturated aqueous NH4Cl (3×75 mL), saturated aqueous NaHCO3 (3×75 mL), and brine (75 mL). The insoluble yellow solid was isolated by filtration to provide the amide (0.150 g, 83%). A mixture of the amide (0.148 g, 0.413 mmol) and 2 M NaOH (7.00 mL) was heated at 85° C. for 19 h, cooled to 5° C., and neutralized with 4 M HCl in dioxanes. The white solid was filtered and rinsed with acetone to provide 5,7-dimethoxy-2-(4-methoxy-3,5-dimethylphenyl)quinazolin-4(3H)-one (0.144 g, 100%). Selected data: 1H NMR (300 MHz, CDCl3) δ 11.00 (s, 1H), 7.90 (s, 2H), 6.74 (d, J=2.33 Hz, 1H), 6.51 (d, J=2.32 Hz, 1H), 3.88 (s, 3H), 3.86 (s, 3H), 3.72 (s, 3H), 2.29 (s, 6H); MS (APCI) m/z 341 [M+H]+.

Workup

  1. washwashed with saturated aqueous NH4Cl (3×75 mL), saturated aqueous NaHCO3 (3×75 mL), and brine (75 mL)
  2. customThe insoluble yellow solid was isolated by filtration

Sources & evidence

ORD record
ord-5354f6a0f1b34df59f4531557e2d39e4
Source dataset
uspto-grants-2015_12
Patent number
US09199990B2

Reaction notes

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