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

HRID 2410024

Reaktionsgleichung

Reaktionsgleichung von HRID 2410024
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1314b3d30f8f4e9188c542534b71b0bb
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815884B2

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