L-Methionine → 8-bromo-3-methyl-2-(methylthio)quinazolin-4(3H)-one

HRID 1056091Notes

Reaction equation

HRID 1056091 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[S:12])[N:8]([CH3:13])[C:7]2=[O:14].[C:15](=O)([O-])[O-].[K+].[K+].N[C@H](C(O)=O)CCSC>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH3:15])[N:8]([CH3:13])[C:7]2=[O:14]

Participants

5

Reactant 3

HCID 6137L-MethionineHCID 11430Potassium CarbonateHCID 897834618-bromo-3-methyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Product 1

HCID 897822298-bromo-3-methyl-2-(methylthio)quinazolin-4(3H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 8-bromo-3-methyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (1.00 g, 3.69 mmol), potassium carbonate (0.510 g, 3.69 mmol), and Met (0.344 mL, 5.53 mmol) in THF (7.0 mL) was stirred at 25° C. for 3d. The mixture was vacuum filtered, and the filtrate was concentrated in vacuo to provide 8-bromo-3-methyl-2-(methylthio)quinazolin-4(3H)-one (1.052 g, 3.69 mmol, 100% yield) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ ppm 8.18 (1H, dd, J=7.9, 1.1 Hz), 7.96 (1H, dd, J=7.6, 1.2 Hz), 7.22 (1H, t, J=7.8 Hz), 3.62 (3H, s), 2.75 (3H, s). m/z (ESI, +ve) 284.9 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a27a137868a24b1f8ea7d3705a0b6b72
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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