Isopropyl iodide → HCID 25214953, compound

HRID 2194755Notes

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[CH:30]([CH3:32])[CH3:31]>CN(C=O)C>[CH: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])([CH3:32])[CH3:31]

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) (5.94 g, 20 mmol) and powdered anhydrous potassium carbonate (3.31 g, 24 mmol) in DMF (40 mL), was added 2-iodopropane (2 mL, 20 mmol). The mixture was then stirred in an oil bath (50-60° C.) overnight and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 700 mg (10%) of 3-(3,5-diisopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (77) as a white solid. m.p. 278-280° C.; 1H-NMR (200 MHz, CDCl3) δ 1.11 (3H, d, J=7.0 Hz), 1.20 (3H, d, J=7.0 Hz), 1.37 (3H, d, J=6.6 Hz), 1.47 (3H, d, J=6.6 Hz), 2.19 (1H, m), 2.54 (3H, s), 3.55 (1H, m), 7.81 (1H, s), 7.98 (1H, s), 8.07 (1H, s), 9.09 (1H, s); m/z (EI) 339 (M+).

Workup

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

Sources & evidence

ORD record: ord-5a19149a2f134de6b729e4d2903aa0f7
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334295B2

Reaction notes

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