Acetic Anhydride → 4-(1-Acetyl-4-piperidinyl)-2-aminoquinazoline

HRID 617178Notes

Reaction equation

HRID 617178 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>CN(C)C=O>[C:25]([N:15]1[CH2:16][CH2:17][CH:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([NH2:1])[N:11]=2)[CH2:13][CH2:14]1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 154287752-Amino-4-(4-piperidinyl)quinazoline

Product 1

HCID 154287764-(1-Acetyl-4-piperidinyl)-2-aminoquinazolineYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold solution of 2-amino-4-(4-piperidyl)quinazoline (500 mg, 2.19 mmol) and triethylamine (233 mg, 2.3 mmol) in N,N-dimethylformamide (10 ml) was added dropwise acetic anhydride (0.22 ml, 2.30 mmol) under a nitrogen atmosphere. The reaction mixture was stirred for about 3 hours and was evaporated. The residue was partitioned between dichloromethane and saturated sodium hydrogencarbonate aqueous solution. The organic layer was washed with water and then dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from ethanol. Recrystallization from methanol gave the titled compound(452 mg).

Workup

  1. customwas evaporated
  2. customThe residue was partitioned between dichloromethane and saturated sodium hydrogencarbonate aqueous solution
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethanol
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-260fcdb2392148ba881ea8ed6c2255f6
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

Loading…