Bromine → HCID 18442554, compound

HRID 458525Notes

Reaction equation

HRID 458525 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][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[CH2:15][CH2:16][CH2:17][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

4

Reactant 2

HCID 24408BromineHCID 18442555HCID 18442555, compound

Product 1

HCID 18442554HCID 18442554, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

3-benzyl-2-propyl-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one (1-2, 0.52 g, 1.93 mmol) was dissolved in AcOH (3.0 mL) and treated with Br2 neat (0.11 mL, 2.13 mmol). The reaction was stirred overnight at 25° C. and then concentrated. The residue was purified by preparative thin layer chromatography (SiO2, 40% EtOAc/hexanes) to yield 3-benzyl-2-(1-bromopropyl)-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one (1-3). 1H NMR (300 MHz, CDCl3) δ 7.33 (m, 4H), 7.26 (d, 1H obscured), 6.15 (d, J=16.1 Hz, 1H), 4.80 (d, J=16.1 Hz, 1H), 4.58 (t, J=7.3 Hz, 1H), 2.92 (m, 4H), 2.36 (m, 1H), 2.12 (m, 3H), 0.69 (t, J=7.3 Hz, 3H). MS 347.0 found 347.3 required.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative thin layer chromatography (SiO2, 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-99cdff039e7a4c788295113dea844e33
Source dataset
uspto-grants-2007_03
Patent number
US07192949B2

Reaction notes

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