Ethyl isocyanatoacetate → HCID 59313214, compound

HRID 2410059Notes

Reaction equation

HRID 2410059 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[CH2:9][C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].C(N(C(C)C)CC)(C)C.[N:27]([CH2:30][C:31]([O:33]CC)=[O:32])=[C:28]=[O:29]>ClCCl>[CH2:13]([N:7]1[C:8]([OH:12])=[C:9]([C:28]([NH:27][CH2:30][C:31]([OH:33])=[O:32])=[O:29])[C:10](=[O:11])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1=[O:17])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 110645171,3-Dibutylpyrimidine-2,4,6(1H,3H,5H)-trione

Product 1

HCID 59313214HCID 59313214, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,3-dibutyl-2,4,6(1H,3H,5H)-pyrimidinetrione (1.3 g mg, 5.5 mmoles) and diisopropylethylamine (1.9 mL, 11.0 mmoles) in dichloromethane (20 mL) was treated with ethyl isocyanatoacetate (673 uL, 6.0 mmoles) and stirred for 24 hours. The mixture was washed with 1 molar hydrochloric acid (×2), dried and evaporated. The residue was taken up in ethanol (5 mL) and treated with 6 molar sodium hydroxide (3 mL) and stirred for 2 hours. The mixture was acidified with 1 molar hydrochloric acid and stirred for 30 minutes to give a solid which was recrystallized from acetic acid-water to afford the title compound (1.2 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.10 (br. s., 1 H), 10.11 (t, J=6.19 Hz, 1 H), 4.13 (d, J=5.81 Hz, 2 H), 3.81 (t, 4 H), 1.43-1.63 (m, 4 H), 1.14-1.41 (m, 4 H), 0.89 (t, J=7.33 Hz, 6 H).

Workup

  1. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  2. customdried
  3. customevaporated
  4. additiontreated with 6 molar sodium hydroxide (3 mL)
  5. stirringstirred for 2 hours
  6. stirringstirred for 30 minutes
  7. customto give a solid which
  8. customwas recrystallized from acetic acid-water

Sources & evidence

ORD record
ord-580a2fc0e5c84b08b605e758c432f7cd
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

Loading…