Hexyl isocyanate → HCID 72548494, compound

HRID 1486540Notes

Reaction equation

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

Participants

Reactant 2

HCID 75659Hexyl isocyanate

HCID 20099778HCID 20099778, compound

Product 1

HCID 72548494HCID 72548494, compoundYield 22%

Conditions

Temperature: 110 °C

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 6, starting from 5-(4-fluorophenyl)-1H-pyrimidine-2,4-dione (0.10 g, 0.48 mmol); 4.5 equivalents of hexyl isocyanate were used herein, splitted into two aliquots (2.2 equiv each) and the reaction mixture was heated under microwave irradiation to 110° C. for 1 hr (2 cycles of 30 min each). The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 84:16) to afford the title compound (0.03 g, 22% over two steps) as white powder. 1H NMR (400 MHz, CDCl3) δ 0.91 (d, J=6.3 Hz, 3H), 1.27-1.42 (m, 6H), 1.58-1.68 (m, 2H), 3.41 (td, J=7.1, 5.6 Hz, 2H), 7.06-7.17 (m, 2H), 7.45-7.63 (m, 2H), 8.35 (s, 1H), 8.55 (s, 1H), 8.93-9.16 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 14.41, 22.33, 26.62, 29.26, 31.38, 41.46, 115.62, 126.97, 130.27, 135.83, 149.57, 150.60, 160.93, 162.81 (d, J=250.5 Hz). MS (ESI) m/z: 207 [M-H]+.

Workup

customdescribed for the synthesis of Example 6
customsplitted into two aliquots (2.2 equiv each)
customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-e6c6fa285fcd4fcf87d2b2cf4ff22893
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428465B2

Reaction notes

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