2-Methoxyethanol → HCID 59359763, compound

HRID 1187259Notes

Reaction equation

HRID 1187259 reaction equation
[H-].[Na+].C([NH:6][C:7]1[N:16]=[C:15](C2N=CNN=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:22])[CH:13]=2)[N:8]=1)(=O)C.[CH3:23][O:24][CH2:25][CH2:26][OH:27]>>[NH2:6][C:7]1[N:16]=[C:15]([O:27][CH2:26][CH2:25][O:24][CH3:23])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:22])[CH:13]=2)[N:8]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 178474427HCID 178474427, compound

Product 1

HCID 59359763HCID 59359763, compoundYield 94%

Procedure

To 2-methoxyethanol (10 ml) was added NaH (80 mg of a 60% dispersion in mineral oil, 2.0 mmol). The mixture was stirred at room temperature for 10 minutes. Then, 2-acetamido-6-bromo-4-(1,2,4-triazolyl)-quinazoline (167 mg, 0.5 mmol) was added to this solution. The resulting mixture was stirred at room temperature for 30 minutes and then heated at 80° C. for 2 hours. The solvents were evaporated in vacuo and the crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1:80), yielding the title compound as a white solid (140 mg, yield: 94%) which was characterized by its mass spectrum as follows: MS (m/z): 298 ([M+H]+, 100).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. temperatureheated at 80° C. for 2 hours
  3. customThe solvents were evaporated in vacuo
  4. customthe crude residue was purified by silica gel flash chromatography
  5. additiona mixture of methanol and dichloromethane (in a ratio of 1:80),

Sources & evidence

ORD record
ord-216189da5792440db38dcb12e6ccb229
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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