Urea → HCID 24830239, compound

HRID 2410043Notes

Reaction equation

HRID 2410043 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH2:11][C:10](=[O:14])[N:9]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]2=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N=C=[O:29])CCCCC1.C1(N)CCCC1.[NH2:36][C:37](N)=[O:38].C(Cl)(=O)[CH2:41][C:42](Cl)=[O:43]>ClCCl>[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:37]([NH:36][CH2:41][C:42]([OH:43])=[O:29])=[O:38])=[C:10]([OH:14])[N:9]([CH:15]3[CH2:16][CH2:17][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 1176UreaHCID 2906CyclopentylamineHCID 18502Cyclohexyl isocyanateHCID 74269Propanedioyl dichlorideHCID 68635820HCID 68635820, compound

Product 1

HCID 24830239HCID 24830239, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1-Cyclohexyl-3-cyclopentyl-2,4,6(1H,3H,5H)-pyrimidinetrione. Cyclohexyl isocyanate (14.7 g, 117.34 mmoles) in dichloromethane (500 mL) under argon was treated with a solution of cyclopentylamine (11.58 mL, 117.34 mmoles) in dichloromethane (300 mL) and stirred overnight to leave a thick suspension of the urea. Malonyl dichloride (12.55 mL, 129 mmoles) in dichloromethane (200 mL) was added and the mixture was heated under gentle reflux for 3.5 hours. The mixture was washed with 1 molar hydrochloric acid (×2) dried and evaporated. Crystallization from ethanol and flash chromatography of the liquors (hexane to ethyl acetate) gave the title compound (18.9 g, 58%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.96-5.12 (m, 1 H), 4.46 (tt, J=12.13, 3.54 Hz, 1 H), 3.69 (s, 2 H), 2.15 (ddd, 2 H), 1.67-2.00 (m, 8 H), 1.41-1.66 (m, 5 H), 1.27 (m, 2 H), 1.11 (m, 1 H).

Workup

  1. customto leave
  2. temperaturethe mixture was heated
  3. temperatureunder gentle reflux for 3.5 hours
  4. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  5. customdried
  6. customevaporated
  7. customCrystallization from ethanol and flash chromatography of the liquors (hexane to ethyl acetate)

Sources & evidence

ORD record
ord-3e560aecd4ad49a7bdf88a0723a9e73b
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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