Hexane → HCID 178525912, compound

HRID 2410030Notes

Reaction equation

HRID 2410030 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH2:11][C:10](=[O:14])[N:9]([CH2:15][CH2:16][CH:17]3[CH2:19][CH2:18]3)[C:8]2=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)CC(Cl)=O.C1([N:34](CCC2CC2)[C:35](N)=[O:36])CCCCC1.CCCCCC.[C:49]([O:52]CC)(=[O:51])[CH3:50].CCCCCC>ClCCl>[CH:1]1([N:7]2[C:12]([OH:13])=[C:11]([C:35]([NH:34][CH2:50][C:49]([OH:52])=[O:51])=[O:36])[C:10](=[O:14])[N:9]([CH2:15][CH2:16][CH:17]3[CH2:18][CH2:19]3)[C:8]2=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 8058HexaneHCID 74269Propanedioyl dichlorideHCID 21226206Ethyl acetate hexaneHCID 68636787HCID 68636787, compoundHCID 68839886HCID 68839886, compound

Product 1

HCID 178525912HCID 178525912, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Cyclohexyl-3-(2-cyclopropylethyl)-2,4,6(1H,3H,5H)-pyrimidinetrione. Malonyl dichloride (250 uL, 2.57 mmoles) was added dropwise to a solution of N-cyclohexyl-N-(2-cyclopropylethyl)urea (500 mg, 2.38 mmoles) in dichloromethane under argon. The mixture was stirred overnight then heated under reflux for 2 hours. Flash chromatography (hexane to 20% ethyl acetate-hexane) gave the title compound (230 mg, 35%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.57-4.71 (m, 1 H), 3.94-4.04 (m, 2 H), 3.60-3.68 (m, 2 H), 2.20-2.36 (m, 2 H), 1.86 (d, J=13.39 Hz, 2 H), 1.60-1.73 (m, 3 H), 1.45-1.60 (m, 2 H), 1.29-1.44 (m, 2 H), 1.15-1.29 (m, 1 H), 0.62-0.77 (m, 1 H), 0.40-0.51 (m, 2 H), −0.00-0.12 (m, 2 H).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-93d7971caf5c49f3aad00baff1122117
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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