Morpholine → 4-Quinazolinamine, 2-(4-morpholinyl)-

HRID 1076359Notes

Reaction equation

HRID 1076359 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[N:17]=[C:16]([NH2:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1>O1CCCC1>[O:4]1[CH2:5][CH2:6][N:1]([C:8]2[N:17]=[C:16]([NH2:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 2528792-Chloroquinazolin-4-amine

Product 1

HCID 6600654-Quinazolinamine, 2-(4-morpholinyl)-Yield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7 g of morpholine in 25 ml of tetrahydrofuran was added dropwise to a solution of 7.2 g of 2-chloro-4-aminoquinazoline in 75 ml of tetrahydrofuran. After the addition was completed, the mixture was heated at reflux overnight. The reaction mixture was evaporated to dryness and the residue was recrystallized twice from ethanol to give 5 g of 2-morpholino-4-aminoquinazoline; m.p. 216°-219°. The following analytical data were obtained.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux overnight
  4. customThe reaction mixture was evaporated to dryness
  5. customthe residue was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-a14c624a0d8449e580f19af0ed656ba0
Source dataset
uspto-grants-1976_05
Patent number
US03956495

Reaction notes

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