Methyl iodide → HCID 131736789, compound

HRID 1486550Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[C:11](=[O:26])[NH:12][C:13](=[O:25])[N:14]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:17])[CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[CH3:28]>>[Si:1]([O:8][CH2:9][C:10]1[C:11](=[O:26])[N:12]([CH3:28])[C:13](=[O:25])[N:14]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:17])[CH:15]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 90032281HCID 90032281, compound

Product 1

HCID 131736789HCID 131736789, compoundYield 37%

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 16 (Step 1), starting from 5-[[tert-butyl(dimethyl)silyl]oxymethyl]-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide (0.14 g, 0.37 mmol); iodomethane was used herein and the reaction was stirred under nitrogen at room temperature for 45 minutes. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 90:10) to afford the title compound (0.055 g, 37%) as a clear, colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.12 (s, 6H), 0.90 (t, J=6.6 Hz, 3H), 0.95 (s, 9H), 1.29-1.41 (m, 6H), 1.57-1.65 (m, 2H), 3.36 (s, 3H), 3.40 (td, J=7.1, 5.7 Hz, 2H), 4.53 (d, J=1.7 Hz, 2H), 8.47 (t, J=1.6 Hz, 1H), 9.32 (t, J=4.5 Hz, 1H). MS (ESI) m/z: 398 [M-H]+.

Workup

customdescribed for the synthesis of Example 16 (Step 1)
customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-deb1f64c71b045989d188386d0084b34
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428465B2

Reaction notes

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