Hexyl isocyanate → HCID 72548492, compound

HRID 1486538Notes

Reaction equation

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

Participants

Reactant 2

HCID 75659Hexyl isocyanate

HCID 118022749HCID 118022749, compound

Product 1

HCID 72548492HCID 72548492, compoundYield 23%

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 1, starting from 3-(cyclopropylmethyl)-5-methyl-1H-pyrimidine-2,4-dione (0.05 g, 0.30 mmol); 1.8 equivalents of hexyl isocyanate were used herein. The crude product was purified by preparative HPLC-MS to afford the title compound (0.02 g, 23%) as colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.36-0.44 (m, 2H), 0.44-0.53 (m, 2H), 0.89 (t, J=6.7 Hz, 3H), 1.17-1.48 (m, 6H), 1.50-1.77 (m, 3H), 2.00 (d, J=1.3 Hz, 3H), 3.38 (td, J=7.1, 5.5 Hz, 2H), 3.86 (d, J=7.2 Hz, 2H), 8.23 (q, J=1.3 Hz, 1H), 9.37 (t, J=5.5 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 4.02, 9.76, 13.47, 14.15, 22.66, 26.70, 29.35, 31.55, 41.34, 46.25, 111.81, 132.62, 150.77, 152.71, 163.16. MS (ESI) m/z: 308 [M-H]+.

Workup

customdescribed for the synthesis of Example 1
customThe crude product was purified by preparative HPLC-MS

Sources & evidence

ORD record: ord-90b66698a2de4170990bbff7cd1716b7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428465B2

Reaction notes

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