4-Chloroquinazolin-6-yl acetate → (R)-4-(1-phenylethylamino)quinazolin-6-yl acetate

HRID 83988Notes

Reaction equation

HRID 83988 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2Cl)(=[O:3])[CH3:2].Cl[C:17]1[CH:18]=[C:19]([C@H:24]([NH2:26])[CH3:25])[CH:20]=[CH:21][C:22]=1F>C(O)(C)C>[C:19]1([C@H:24]([NH:26][C:8]2[C:7]3[C:12](=[CH:13][CH:14]=[C:5]([OH:4])[CH:6]=3)[N:11]=[CH:10][N:9]=2)[CH3:25])[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=1.[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[NH:26][C@@H:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=1)[CH3:25])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 189676244-Chloroquinazolin-6-yl acetateHCID 28602988(R)-1-(3-Chloro-4-fluorophenyl)ethanamine

Product 2

HCID 66755670(R)-4-(1-phenylethylamino)quinazolin-6-yl acetateYield 89.7%HCID 66756048(R)-4-(1-Phenylethylamino)quinazolin-6-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of compound 0204 (1.0 g, 4.5 mmol) and (R)-1-(3-chloro-4-fluoro-phenyl)ethanamine (0.87 g, 5.0 mmol) in isopropanol (45 mL) was stirred at 90° C. for 1 hour. The mixture was cooled to room temperature and the resulting precipitate was isolated. The solid was washed in turn with isopropanol and methanol, dried to provide the title compound (R)-4-(1-phenylethylamino)quinazolin-6-yl acetate as a yellow solid (0.62 g, 61%): LCMS 308 [M+1]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe resulting precipitate was isolated
  3. washThe solid was washed in turn with isopropanol and methanol
  4. customdried

Sources & evidence

ORD record
ord-08feaa61083e4e36800ab32b8c74f444
Source dataset
uspto-grants-2014_09
Patent number
US08846912B2

Reaction notes

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