Hexyl isocyanate → HCID 90032281, compound

HRID 1486549Notes

Reaction equation

HRID 1486549 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11](=[O:17])[NH:12][C:13](=[O:16])[NH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:18]([N:24]=[C:25]=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CN(C1C=CN=CC=1)C>[Si:1]([O:8][CH2:9][C:10]1[C:11](=[O:17])[NH:12][C:13](=[O:16])[N:14]([C:25]([NH:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:26])[CH:15]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 75659Hexyl isocyanateHCID 90018675HCID 90018675, compound

Product 1

HCID 90032281HCID 90032281, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The title compound: was obtained according to the procedure described for the synthesis of Example 1, starting from 5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1H-pyrimidine-2,4-dione (0.28 g, 1.08 mmol); 2.2 equiv of DMAP and 2.2 equiv of hexyl isocyanate were used herein. The reaction was here stirred for 66 hrs, and the crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 75:25) to afford the title compound (0.30 g, 73%) as a white solid. 1H NMR (400 MHz, CDCl3); δ 0.12 (s, 6H), 0.89 (t, J=6.9 Hz, 3H), 0.94 (s, 9H), 1.29-1.39 (m, 6H), 1.58-1.63 (m, 2H), 3.39 (td, J=7.1, 5.7 Hz, 2H), 4.52 (d, J=1.7 Hz, 2H), 828 (s, 1H), 8.47 (t, J=1.7 Hz, 1H), 9.06 (t, J=4.8 Hz, 1H). MS (ESI) m/z: 384 [M-H]+.

Workup

  1. customdescribed for the synthesis of Example 1
  2. customthe crude was purified by column chromatography

Sources & evidence

ORD record
ord-5d6b01236ef84015992d2ce4cac82e4e
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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