Butyl iodide → 3-{[3-Butyl-5-(1-methylethyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]carbonyl}-5-methylbenzonitrile

HRID 2194757Notes

Reaction equation

[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[C:17]#[N:18])=[O:13])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:30][CH2:31][CH2:32][CH3:33]>CN(C=O)C>[CH2:30]([N:6]1[C:5]([C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:17]#[N:18])=[O:13])=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9](=[O:10])[NH:8][C:7]1=[O:11])[CH2:31][CH2:32][CH3:33]

Participants

Conditions

Temperature: 55 °C

Procedure

To a stirred mixture of 3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (Compound 1) (2.97 g, 10 mmol) and powdered anhydrous potassium carbonate (1.66 g, 12 mmol) in DMF (20 mL), was added iodobutane (1.37 mL, 12 mmol). The mixture was then stirred in an oil bath (50-60° C.) for 24 hr. and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 1.78 g (50%) of 3-(3-butyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (47) as a white foam. 1H-NMR (200 MHz, CDCl3) δ 0.80 (3H, d, J=3.2 Hz), 0.83 (3H, d, J=3.2 Hz), 1.12 (3H, d, J=7.0 Hz), 1.23 (3H, d), J=7.0 Hz), 1.90 (1H, m), 2.25 (1H, m), 2.53 (3H, s), 2.93 (1H, dd, J=14.2 Hz, J=7.4 Hz), 3.75 (1H, dd, J=14.2 Hz, J=7.4 Hz), 7.80 (1H, s), 7.92 (1H, s), 8.03 (1H, s), 9.03 (1H, s); m/z (EI) 353 (M+).

Workup

customand evaporated in vacuo
customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2))

Sources & evidence

ORD record: ord-d4dba53227324bcba7f130d15804655a
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334295B2

Reaction notes

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