Ethylamine → N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl) N-ethylamine

HRID 2081976Notes

Reaction equation

HRID 2081976 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[NH:7][C:6]2=[O:14].[CH2:15]([NH2:17])[CH3:16]>C(#N)C>[CH3:13][C:8]1[NH:7][C:6](=[O:14])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][NH:17][CH2:15][CH3:16])[CH:4]=2)[N:9]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 1354425816-(Bromomethyl)-2-methyl-4(1H)-quinazolinone

Product 1

HCID 136093134N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl) N-ethylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-bromomethyl-3,4-dihydro-2-methylquinazolin-4-one (prepared as described in Example 3; 10 g), anhydrous ethylamine (7.9 ml) and acetonitrile (250 ml) was stirred rapidly at laboratory temperature for 4 hours. The mixture was evaporated to dryness, the residue was dissolved in water, filtered and the filtrate was evaporated. The residue was triturated in acetone to give N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-ethylamine, as its hydrobromide salt (8.5 g), m.p. >260° C.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in water
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue was triturated in acetone

Sources & evidence

ORD record
ord-f181719081fe44618e84cd028debbec5
Source dataset
uspto-grants-1993_02
Patent number
US05187167

Reaction notes

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