Water → HCID 71654963, compound

HRID 1486528Notes

Reaction equation

HRID 1486528 reaction equation
[C:1]([C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1)#[N:2].[CH2:11]([N:17]=[C:18]=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O>N1C=CC=CC=1>[C:1]([C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[N:7]([C:18]([NH:17][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:19])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 75659Hexyl isocyanateHCID 781455-Cyanouracil

Product 1

HCID 71654963HCID 71654963, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

5-Cyanouracil (0.10 g, 0.73 mmol) was dissolved in dry pyridine (5.0 mL) and hexyl isocyanate (0.08 mL, 1.10 mmol) was added. The mixture was heated under microwave irradiation to 100° C. for 10 min and then was poured into water (50 mL). The product was extracted with dichloromethane (2×50 mL), the combined organic layers were dried over Na2SO2 and the solvent was concentrated under reduced pressure. The crude was purified by column chromatography using SI (2 g) cartridge (dichloromethane) and subsequently washed with warm heptane to afford the title compound (0.03 g, 16%) as white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.86-0.96 (m, 3H), 1.29-1.41 (m, 6H), 1.57-1.70 (m, 2H), 3.44 (q, J=6.4, 2H), 5.01 (s, 1H), 8.85 (br s, 1H), 9.05 (s, 1H). MS (ESI) m/z: 263 [M-H]−.

Workup

  1. extractionThe product was extracted with dichloromethane (2×50 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO2
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe crude was purified by column chromatography
  5. washsubsequently washed with warm heptane

Sources & evidence

ORD record
ord-f94b4d4fedc44fb39421c1303557157c
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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