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

반응식

HRID 2410024 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-1314b3d30f8f4e9188c542534b71b0bb
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815884B2

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