1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(3,4-dimethoxybenzyl)-6-bromo-1,5-dimethylpyrimidine-2,4(1H,3H)-dione

HRID 514314Notes

Reaction equation

N12CCCN=C1CCCCC2.[Br:12][C:13]1[N:18]([CH3:19])[C:17](=[O:20])[NH:16][C:15](=[O:21])[C:14]=1[CH3:22].Cl[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1>C(#N)C>[Br:12][C:13]1[N:18]([CH3:19])[C:17](=[O:20])[N:16]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=2)[C:15](=[O:21])[C:14]=1[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (98%, 5.57 mL, 36.5 mmol) was added to a suspension of C2 (4.00 g, 18.3 mmol) and 4-(chloromethyl)-1,2-dimethoxybenzene (5.16 g, 27.6 mmol) in acetonitrile (80 mL), and the reaction mixture was heated at 60° C. for 18 hours. After removal of solvent in vacuo, the residue was purified via silica gel chromatography (Gradient: 25% to 50% ethyl acetate in heptane) to afford the product as a white solid. Yield: 5.70 g, 15.4 mmol, 84%. 1H NMR (400 MHz, CDCl3) δ 7.08-7.12 (m, 2H), 6.80 (d, J=8.0 Hz, 1H), 5.07 (s, 2H), 3.88 (s, 3H), 3.85 (s, 3H), 3.65 (s, 3H), 2.14 (s, 3H).

Workup

customAfter removal of solvent in vacuo
customthe residue was purified via silica gel chromatography (Gradient: 25% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-d85c5822c5a74c3e9607145c9efbda6f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107923B2

Reaction notes

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