Hexyl isocyanate → N-hexyl-2,4-dioxo-5-(3-pyridyl)pyrimidine-1-carboxamide

HRID 1486555Notes

Reaction equation

HRID 1486555 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=2)[CH:2]=1.[CH2:15]([N:21]=[C:22]=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:15]([NH:21][C:22]([N:11]1[CH:12]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:8](=[O:14])[NH:9][C:10]1=[O:13])=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 75659Hexyl isocyanateHCID 122449965-(pyridin-3-yl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 72548974N-hexyl-2,4-dioxo-5-(3-pyridyl)pyrimidine-1-carboxamideYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The title compound was obtained according, to the procedure described for the synthesis of Example 1, starting from 5-(3-pyridyl)-1H-pyrimidine-2,4-dione (0.067 g, 0,198 mmol). Herein, 2 equivalents of DMAP and 2.7 equivalents of hexyl isocyanate in 4 mL pyridine were used. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 40:60) to afford the title compound (0.04 g, 57%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.90 (t, J=6.0 Hz, 3H), 1.29-1.41 (m, 6H), 1.58-1.67 (m, 2H), 3.42 (dt, J=7.1, 5.5 Hz, 2H), 7.37 (ddd, J=8.0, 4.9, 0.9 Hz, 1H), 7.97 (td, J=8.0, 2.0 Hz, 1H), 8.64 (dd, J=4.9, 1.7 Hz, 1H), 8.66 (s, 1H), 8.80 (dd, J=2.4, 0.9 Hz, 1H), 9.11 (t, J=5.0 Hz, 1H), 9.21 (s, 1H). 13C NMR (101 MHz, CDCl3): δ 14.13, 22.66, 26.64, 29.29, 31.51, 41.58, 77.16, 113.74, 123.50, 127.93, 136.39, 136.58, 148.70, 149.48, 149.74, 151.09, 161.30. MS (ESI) m/z: 317 (M-Hr.

Workup

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

Sources & evidence

ORD record
ord-df8a2bf1174845f3af8c6b418f9b6065
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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