Benzoyl chloride → HCID 72548491, compound

HRID 1486539Notes

Reaction equation

HRID 1486539 reaction equation
[CH2:1]([NH:7][C:8]([N:10]1[CH:15]=[C:14]([NH:16][CH3:17])[C:13](=[O:18])[NH:12][C:11]1=[O:19])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:20]([N:16]([CH3:17])[C:14]1[C:13](=[O:18])[NH:12][C:11](=[O:19])[N:10]([C:8]([NH:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:9])[CH:15]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 71654964HCID 71654964, compound

Product 1

HCID 72548491HCID 72548491, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-hexyl-5-methylamino-2,4-dioxo-pyrimidine-1-carboxamide (0.08 g, 0.30 mmol) was dissolved in dry pyridine (4 mL). To the resulting solution, benzoyl chloride (0.04 mL, 0.39 mmol) was added. The reaction was stirred at room temperature under nitrogen atmosphere for 18 hrs, then concentrated under reduced pressure. The crude was purified by column chromatography using SI (5 g) cartridge (cyclohexane:EtOAc 84:16) to afford the title compound (0.05 g, 45%) as colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.89 (t, J=6.9 Hz, 3H), 1.28-1.33 (m, 6H), 1.53-1.59 (m, 2H), 3.29 (s, 3H), 3.34 (dt, J=5.7, 7.0 Hz, 2H), 7.33-7.43 (m, 5H), 8.22 (br s, 1H), 8.31 (br s, 1H) 8.88 (t, J=5.7 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 13.96, 22.48, 26.44, 29.04, 31.31, 37.17, 41.41, 121.47, 127.17, 128.43, 130.27, 135.29, 137.63, 149.03, 150.05, 159.01, 171.78. MS (ESI) m/z: 371 [M-H]−.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-d541c3b7b16445bfb924480dc3f3cf13
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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