Methanol → HCID 86723623, compound

HRID 1474073Notes

Reaction equation

HRID 1474073 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:29])[N:6]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([C@@H:13]([NH:15]C(=O)OC(C)(C)C)[CH3:14])=[N:8]2.B(Br)(Br)Br.CO>C(Cl)Cl>[NH2:15][C@H:13]([C:7]1[N:6]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:5](=[O:29])[C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[OH:2])[N:8]=1)[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 86723624HCID 86723624, compound

Product 1

HCID 86723623HCID 86723623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (S)-tert-butyl (1-(5-methoxy-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethyl)carbamate (100 mg, 0.25 mmol) in DCM (3 mL) at −78° C. was added BBr3 (1M/DCM, 0.63 mL, 0.63 mmol). The reaction was stirred at −78° C. for 20 min, then warmed to ambient temperature. After stirring 10 minutes at ambient temperature, MeOH (5 mL) was added. The reaction was concentrated in vacuo. Purification by flash chromatography (12 g silica, 0-100% EtOAc/DCM then 0-30% MeOH/DCM) provided (S)-2-(1-aminoethyl)-5-hydroxy-3-phenylquinazolin-4(3H)-on as an orange residue. ES/MS 282.1 (M+H+).

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringAfter stirring 10 minutes at ambient temperature
  3. concentrationThe reaction was concentrated in vacuo
  4. customPurification by flash chromatography (12 g silica, 0-100% EtOAc/DCM

Sources & evidence

ORD record
ord-b97084462bea4bfc95591eb433a9f15f
Source dataset
uspto-grants-2015_04
Patent number
US09018221B2

Reaction notes

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