Aminoacetaldehyde dimethyl acetal → HCID 20093975, compound

HRID 273804Notes

Reaction equation

HRID 273804 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[N:5]=[C:4]([CH3:13])[N:3]=1.[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH2:18]>O1CCCC1>[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH:18][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[N:5]=[C:4]([CH3:13])[N:3]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetal2×HCID 200939884-Chloro-2,5-dimethylquinazoline

Product 1

HCID 20093975HCID 20093975, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

4. 14.15 g of crude 4-chloro-2,5-dimethylquinazoline are suspended in 300 ml of tetrahydrofuran, cooled to 5° C. and treated with 16.5 ml of 2,2-dimethoxyethylamine while stirring. The mixture is stirred at room temperature for 24 h., a further 10 ml of 2,2-dimethoxyethylamine are added thereto and the mixture is stirred for a further 40 h. The reaction mixture is evaporated in vacuum and the residue is partitioned between chloroform and saturated aqueous sodium hydrogen carbonate solution. The chloroform solution is evaporated in a vacuum. The residue (21 g) is chromatographed over 150 g of silica gel. 1.85 g of 4-(2,2-dimethoxyethylamino)-2,5-dimethylquinozoline are eluted with ethyl acetate. These are recrystallized from hexane. There are obtained 18.3 g of 4-(2,2-dimethoxyethyl-amino)-2,5-dimethylquinazoline of m.p. 48°-49° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 24 h.
  2. stirringthe mixture is stirred for a further 40 h
  3. customThe reaction mixture is evaporated in vacuum
  4. customthe residue is partitioned between chloroform and saturated aqueous sodium hydrogen carbonate solution
  5. customThe chloroform solution is evaporated in a vacuum
  6. customThe residue (21 g) is chromatographed over 150 g of silica gel
  7. wash1.85 g of 4-(2,2-dimethoxyethylamino)-2,5-dimethylquinozoline are eluted with ethyl acetate
  8. customThese are recrystallized from hexane

Sources & evidence

ORD record
ord-3b6096abbc7c43bab331f6400489e532
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

Loading…