Methanol → HCID 86723623, compound

HRID 1777707Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([C:10]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18](=[O:26])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:27]C)[N:11]=1)[CH3:9])(C)(C)C.B(Br)(Br)Br.CO>C(Cl)Cl>[NH2:7][C@H:8]([C:10]1[N:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:18](=[O:26])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[OH:27])[N:11]=1)[CH3:9]

Participants

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

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

Sources & evidence

ORD record: ord-bc40ef51b4fe439f9b90ef1c8f1f702b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266878B2

Reaction notes

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