4-Bromobenzoyl chloride → N-[1-(3-Benzyl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)propyl]-4-bromo-N-[2-(dimethylamino)ethyl]benzamide

HRID 2224096Notes

Reaction equation

[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[S:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[CH:18]([NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>ClCCCl.C(Cl)Cl>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[S:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[CH:18]([N:21]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[C:32](=[O:33])[C:31]1[CH:35]=[CH:36][C:28]([Br:27])=[CH:29][CH:30]=1)[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

3-Benzyl-2-(1-{[2-(dimethylamino)ethyl]amino}propyl)thieno[3,2-d]pyrimidin-4(3H)-one (1-7, 0.030 g, 0.081 mmol) was dissolved in DCE (1.0 mL) and treated successively with 4-bromo-benzoylchloride (0.026 g, 0.12 mmol) and TEA (0.03 mL, 0.24 mmol). The reaction was stirred at 25° C. for 1 h. The reaction was diluted with DCM (10 mL), washed with 5% NaHCO3 and dried over MgSO4. The organics were concentrated under reduced pressure and subjected to flash column chromatography (SiO2, 0-6% MeOH/CH2Cl2 gradient) to provide N-[1-(3-benzyl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)propyl]-4-bromo-N-[2-(dimethylamino)ethyl]benzamide (1-8). 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=5.2 Hz, 1H), 7.54 (m, 2H), 7.32 (m, 5H), 7.15 (m, 2H), 6.11 (d, J=16.0 Hz, 1H), 5.96 (t, J=7.0 Hz, 1H), 5.12 (d, J=16.0 Hz, 1H), 3.40 (m, 2H), 2.04 (m, 2H), 1.85 (m, 1H), 1.77 (s, 6H), 1.59 (m, 1H), 0.65 (t, J=6.9 Hz, 3H); MS 553.1 found, 553.5 required.

Workup

washwashed with 5% NaHCO3
dry with materialdried over MgSO4
concentrationThe organics were concentrated under reduced pressure

Sources & evidence

ORD record: ord-6c160bc5f1134c3496b1128c591f9e70
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378411B2

Reaction notes

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