2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 20286466, compound

HRID 127291Notes

Reaction equation

HRID 127291 reaction equation
[NH2:1][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]=[C:4]([Cl:16])[N:3]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:27](=[O:28])[CH2:26][CH2:25][C:24]2=[O:29])[CH2:19][CH2:18]1>C(O)CC(C)C>[ClH:16].[NH2:1][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]=[C:4]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:24](=[O:29])[CH2:25][CH2:26][C:27]3=[O:28])[CH2:19][CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 128225521-(Piperidin-4-yl)pyrrolidine-2,5-dione

Product 1

HCID 20286466HCID 20286466, compound

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

The mixture of 215 g of 4-amino-2-chloro-6,7-dimethoxyquinazoline, 192.3 g of 1-(4-piperidinyl)-pyrrolidine-2,5-dione and 5,600 ml of isoamyl alcohol is stirred and refluxed for 22 hours. It is cooled to 20°, filtered and the residue washed once with 250 ml of cold ethanol and twice with 250 ml of diethyl ether each. The solids are suspended in 6000 ml of ethanol and 300 ml of water, the suspension heated to reflux, immediately cooled to 20° and filtered. The residue is washed with 300 ml of cold ethanol and 200 ml of diethyl ether, to yield the 1-[1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-piperidinyl]-pyrrolidin-2,5-dione hydrochloride melting at 237° with decomposition.

Workup

  1. temperaturerefluxed for 22 hours
  2. temperatureIt is cooled to 20°
  3. filtrationfiltered
  4. washthe residue washed once with 250 ml of cold ethanol and twice with 250 ml of diethyl ether each
  5. temperature300 ml of water, the suspension heated
  6. temperatureto reflux
  7. temperatureimmediately cooled to 20°
  8. filtrationfiltered
  9. washThe residue is washed with 300 ml of cold ethanol and 200 ml of diethyl ether

Sources & evidence

ORD record
ord-89075d66179540e2940f2fb1683ef997
Source dataset
uspto-grants-1981_03
Patent number
US04255429

Reaction notes

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