Water → HCID 118023699, compound

HRID 1486536

Reaction equation

HRID 1486536 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.C[C:14]1[C:15](=[O:22])[NH:16][C:17](=[O:21])[NH:18][C:19]=1[CH3:20].[CH2:23]([NH2:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O.N1C=CC=C[CH:32]=1>>[CH2:23]([NH:29][C:17]([N:18]1[C:19]([CH3:20])([CH3:32])[CH2:14][C:15](=[O:22])[NH:16][C:5]1=[O:11])=[O:21])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 5

HCID 962WaterHCID 1049Pyridine2×HCID 8102HexylamineHCID 94429TriphosgeneHCID 960315,6-Dimethyluracil

Product 1

HCID 118023699HCID 118023699, compoundYield 6%

Conditions

Temperature
0 °C

Procedure

Triphosgene (0.12 g, 0.71 mmol) was added to dry pyridine (2.0 mL) at 0° C. The mixture was stirred for 10 min, then a solution of 5,6-dimethyluracil (0.10 g, 0.71 mmol) in dry pyridine (3.0 mL) was added dropwise. The pale yellow suspension formed was stirred at room temperature for 5 hrs, then cooled to 0° C. before adding hexylamine (0.10 mL, 0.71 mmol). The reaction mixture was stirred at room temperature for 18 hrs. Water (30 mL) was added, and the product extracted with EtOAc (3×30 mL). The combined organic layer was dried over Na2SO4 and the solvent removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 90:10) to afford the title compound (0.02 g, 6%) as white powder. 1H NMR (400 MHz, CDCl3) δ 0.90 (t, J=6.6 Hz, 3H), 1.25-1.38 (m, 6H), 1.53-1.67 (m, 2H), 1.83 (br s, 3H), 2.19 (br s, 3H), 3.30 (dt, J=5.6, 70 Hz, 2H), 7.42-7.65 (m, 1H), 9.68 (br s, 1H). 13C NMR (101 MHz, CDCl3): δ 9.00, 13.34, 15.77, 22.35, 26.12, 28.91, 31.30, 40.70, 104.68, 146.24, 149.35, 162.15, 164.20. MS (ESI) m/z: 266 [M-H]−.

Workup

  1. customThe pale yellow suspension formed
  2. stirringwas stirred at room temperature for 5 hrs
  3. stirringThe reaction mixture was stirred at room temperature for 18 hrs
  4. extractionthe product extracted with EtOAc (3×30 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. customthe solvent removed under reduced pressure
  7. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-c3ee702f772b49faa21602fe5dfc1f54
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Linked notes

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