[1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl]-carbamic acid benzyl ester → 2-(1-amino-propyl)-5-methyl-3-phenyl-3H-quinazolin-4-one

HRID 2042858Notes

Reaction equation

HRID 2042858 reaction equation
C(OC(=O)[NH:10][CH:11]([C:14]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22](=[O:30])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:31])[N:15]=1)[CH2:12][CH3:13])C1C=CC=CC=1>C(O)C.[Pd]>[NH2:10][CH:11]([C:14]1[N:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:22](=[O:30])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:31])[N:15]=1)[CH2:12][CH3:13]

Participants

4

Reactant 1

HCID 59841071[1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl]-carbamic acid benzyl ester

Product 1

HCID 598410382-(1-amino-propyl)-5-methyl-3-phenyl-3H-quinazolin-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A catalytic amount of 10% Pd/C was added to a solution of compound 16 (691 mg, 1.62 mmol) in ethanol (8 mL). The resulting mixture was placed under a hydrogen atmosphere (balloon pressure) and allowed to stir at ambient temperature overnight. The reaction was filtered, and the filtrate concentrated in vacuo. The resulting crude residue was purified by flash chromatography to afford the free amine, compound 17, as a pale yellow oil. (ES): m/z 294 (M+H), 237. 1H NMR MHz, DMSO-d6) δ 7.68 (t, 1H, J=7.7 Hz), 7.49-7.63 (m, 3H), 7.43-7.49 (m, 1H), 7.36-7.43 (m, 1H), 7.19-7.34 (m, 2H), 4.03-4.19 (m, 1H), 2.72 (s, 3H), 2.04 (br. s, 2H), 1.63-1.79 (m, 1H), 1.29-1.44 (m, 1H), 0.68 (t, 3H, J=7.3 Hz). The reaction described above and compound 17 are shown below.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6dcc3735e15b4407897e3846593fec63
Source dataset
uspto-grants-2013_11
Patent number
US08586597B2

Reaction notes

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