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

反応式

HRID 2410024 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-1314b3d30f8f4e9188c542534b71b0bb
出典データセット
uspto-grants-2014_08
特許番号
US08815884B2

関連ノート

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