Hexyl isocyanate → HCID 72548495, compound

HRID 1486541Notes

Reaction equation

HRID 1486541 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.[CH2:17]([N:23]=[C:24]=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[CH2:17]([NH:23][C:24]([N:13]1[CH:14]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:10](=[O:16])[NH:11][C:12]1=[O:15])=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 75659Hexyl isocyanateHCID 9016995-(4-Methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 72548495HCID 72548495, compoundYield 17%

Conditions

Temperature
100 °C

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 6, starting from 5-(4-methoxyphenyl)-1H-pyrimidine-2,4-dione (0.06 g, 0.27 mmol); 5.4 equivalents of hexyl isocyanate were used herein, splitted into three aliquots (1.8 equiv each) and the reaction mixture was heated under microwave irradiation to 100° C. for 1 hr (3 cycles of 20 min each). The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 80:20) to afford the title compound (0.02 g, 17% over two steps) as white powder. 1H NMR (400 MHz, CDCl3) δ 0.90 (d, J=6.8 Hz, 3H), 1.29-1.43 (m, 6H), 1.58-1.67 (m, 2H), 3.41 (td, J=7.1, 5.5 Hz, 2H), 3.83 (s, 3H), 6.89-7.00 (m, 2H), 7.41-7.57 (m, 2H), 8.46 (s, 1H), 8.51 (s, 1H), 9.11 (t, J=5.5 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 14.63, 22.47, 26.85, 29.26, 31.63, 41.34, 55.37, 11414, 116.32, 123.66, 129.39, 134.34, 149.83, 150.71, 159.87, 161.58.

Workup

  1. customdescribed for the synthesis of Example 6
  2. customsplitted into three aliquots (1.8 equiv each)
  3. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-958964a34f6e45cf9923abac05b96b63
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

Loading…