Hydrazine → 4-Hydrazinyl-6,7-dimethoxyquinazoline

HRID 1784380Notes

Reaction equation

HRID 1784380 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:16][NH2:17]>C1COCC1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[NH:16][NH2:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 202638104-Hydrazinyl-6,7-dimethoxyquinazolineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-Chloro-6,7-dimethoxy-quinazoline (0.20 g, 0.89 mmol) in anhydrous THF (0.5 ml) was added hydrazine (1M in THF, 2.0 ml, 2.0 mmol). The mixture was stirred at room temperature for 16 hours whereupon a precipitate had formed which was removed by filtration and washed with cold THF to give the desired product (177 mg, 91%) as a sticky off white solid which was sufficiently pure to be used without any further purification. m/z (LC-MS, ESP): 221 [M+H]+, R/T=2.48 mins.

Workup

  1. customhad formed which
  2. customwas removed by filtration
  3. washwashed with cold THF

Sources & evidence

ORD record
ord-a30a485362424c4b8517d06d2a1f8278
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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