Sodium methanethiolate → 5-Methyl-4-(methylthio)quinazoline

HRID 900314Notes

Reaction equation

HRID 900314 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH3:15])[N:8]=[CH:7][N:6]=1>C1COCC1>[CH3:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:5]([S:2][CH3:1])=[N:6][CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 134955764-Chloro-5-methylquinazoline

Product 1

HCID 587117225-Methyl-4-(methylthio)quinazolineYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium thiomethoxide (0.806 g, 11.5 mmol) in THF (40 ml) at 0° C. was added 1B (1.368 g, 7.66 mmol) in THF (25 ml). The mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated to about 15 ml, and water (100 ml) was added. The slurry was stirred at 0° C. for 30 min. The solid was collected by filtration, washed with water and dried to give 1C (1.209 g, 83%) as a solid. The compound has an analytical HPLC retention time=1.899 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm) and a LC/MS M++H=191+.

Workup

  1. concentrationThe reaction mixture was concentrated to about 15 ml, and water (100 ml)
  2. additionwas added
  3. stirringThe slurry was stirred at 0° C. for 30 min
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-177bfe13151f4c33ae9dec1b283ce537
Source dataset
uspto-grants-2008_04
Patent number
US07358256B2

Reaction notes

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