Ethyl isocyanatoacetate → N-{[1-[(3-Cyanophenyl)methyl]-6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine

HRID 2410024Notes

Reaction equation

HRID 2410024 reaction equation
[OH:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4](=[O:16])[C:3]=1[C:17]([NH:19][CH2:20][C:21]([O:23]CC)=[O:22])=[O:18].[N:26]([CH2:29][C:30](OCC)=O)=C=O.[C:35]1([CH2:41]N2C(=O)CC(=O)NC2=O)[CH:40]=C[CH:38]=[CH:37][CH:36]=1.C(N(C(C)C)C(C)C)C>ClCCl>[C:29]([C:30]1[CH:40]=[C:35]([CH2:41][N:7]2[C:2]([OH:1])=[C:3]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[C:4](=[O:16])[N:5]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]2=[O:8])[CH:36]=[CH:37][CH:38]=1)#[N:26]

Participants

6

Reactant 4

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 2687261-benzylpyrimidine-2,4,6(1H,3H,5H)-trioneHCID 178472773HCID 178472773, compound

Product 1

HCID 68635462N-{[1-[(3-Cyanophenyl)methyl]-6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycineYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl N-{[6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycinate. Ethyl isocyanatoacetate (2.24 mL, 20 mmoles) was added dropwise to a solution of 1-(phenylmethyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (4.4 g, 20 mmoles) and ethyl diisopropylamine (6.9 mL, 40 mmoles) in dichloromethane (120 mL) and stirred overnight under argon. The mixture was washed with 1 molar hydrochloric acid, water and brine, dried and evaporated. The solid was slurried in diethyl ether, collected, washed with diethyl ether and hexane, dried to give the title compound (5.1 g, 73%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.13 (br. s., 1 H), 9.84 (br. s., 1 H), 7.13-7.48 (m, 5 H), 4.95 (s, 2 H), 4.17 (d, 2 H), 4.15 (q, 2 H), 1.21 (t, J=7.20 Hz, 3 H)

Workup

  1. washThe mixture was washed with 1 molar hydrochloric acid, water and brine
  2. customdried
  3. customevaporated
  4. customcollected
  5. washwashed with diethyl ether and hexane
  6. customdried

Sources & evidence

ORD record
ord-1314b3d30f8f4e9188c542534b71b0bb
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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