Sodium hydride → HCID 23658469, compound

HRID 1187260Notes

Reaction equation

HRID 1187260 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]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=3)[CH:13]=2)[N:8]=1)(=O)C>C(O)(C)C>[NH2:6][C:7]1[N:16]=[C:15]([O:28][CH:25]([CH3:26])[CH3:24])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=3)[CH:13]=2)[N:8]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178488516HCID 178488516, compound

Product 1

HCID 23658469HCID 23658469, compoundYield 165%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To isopropanol (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-(3,4-dimethoxyphenyl)-4-(1,2,4-triazolyl)-quinazoline (195 mg, 0.5 mmol) was added. The resulting mixture was stirred at room temperature for another 20 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 isopropanol/dichloromethane (in a volume ratio of 1:50), yielding the title compound (140 mg, yield: 82%) as a white solid was characterized by its mass spectrum as follows: MS (m/z): 340 ([M+H]+, 100).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for another 20 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 isopropanol/dichloromethane (in a volume ratio of 1:50),

Sources & evidence

ORD record
ord-a5455930ed5b47e5a26921e0455ecbb4
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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