Ammonia → 2-Chloroquinazolin-4-amine

HRID 471500Notes

Reaction equation

HRID 471500 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) δ 7.52-7.48 (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-df58c119e0ad47d8b870f6e7004a912d
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

Loading…