Bromine → HCID 54758218, compound

HRID 2224094Notes

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[CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21]Br>CC(O)=O>[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]([Br:21])[CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-Benzyl-2-propylthieno[3,2-d]pyrimidin-4(3H)-one (1-5, 0.80 g, 2.81 mmol) was dissolved in AcOH (3.0 mL) and treated with Br2 neat 0.43 mL, 8.44 mmol). The reaction was warmed to 60° C. for 6 h, and then concentrated. The residue was purified by flash column chromatography (SiO2, 0-10% EtOAc/hexanes gradient) to give 3-benzyl-2-(1-bromopropyl)thieno[3,2-d]pyrimidin-4(3H)-one (1-6). 1H NMR (300 MHz, CDCl3) δ 7.82 (d, J=5.2 Hz, 1H), 7.28 (m, 4H), 7.15 (d, J=7.0 Hz, 2H), 6.26 (d, J=16.5 Hz, 1H), 4.93 (d, J=16.5 Hz, 1H), 4.68 (t, J=7.1 H, 1H), 2.43 (m, 1H), 2.25 (m, 1H), 0.73 (t, J=7.0 Hz, 3H); MS 364.8 found 363.2 required.

Workup

concentrationconcentrated
customThe residue was purified by flash column chromatography (SiO2, 0-10% EtOAc/hexanes gradient)

Sources & evidence

ORD record: ord-45586596075c406bbbbb33241ec77a93
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378411B2

Reaction notes

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