Ammonia → 2-Chloroquinazolin-4-amine

HRID 44369

Reaction equation

HRID 44369 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:13]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:11]=[C:10]([NH2:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 2528792-Chloroquinazolin-4-amineYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dichloroquinazoline (2.0 g, 10 mmol) in THF (10 mL), was added ammonia (28-30% in water, 18 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and evaporated. The resulting solid was washed with EtOAc to give the title compound (1.3 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ7.52-7.48 (m, 1H), 7.6-7.58 (m, 1H), 7.8-7.76 (m, 1H), 8.22-8.20 (m, 1H), 8.32 (bs, 2H).

Workup

  1. washwashed with saturated NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. washThe resulting solid was washed with EtOAc

Sources & evidence

ORD record
ord-0a687d3bfdb04c43b9ca57ac7844f968
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Linked notes

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