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Potassium Carbonate → Ethyl 4-((3-((tert-butoxycarbonyl)amino)phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate

HRID 527392
ノート
印刷プレビュー

反応式

HRID 527392 の反応式
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:17]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=[C:19]([S:28][CH3:29])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:4]([O:3][C:1]([NH:8][C:9]1[CH:10]=[C:11]([NH:15][C:21]2[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][N:18]=[C:19]([S:28][CH3:29])[N:20]=2)[CH:12]=[CH:13][CH:14]=1)=[O:2])([CH3:7])([CH3:6])[CH3:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

生成物 1

HCID 57343535Ethyl 4-((3-((tert-butoxycarbonyl)amino)phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
80 °C

実験手順

A mixture of N-Boc-m-phenylenediamine (50a, prepared according to the procedures reported in: Duceppe, J.-S. et al. Org. Process. Res. Dev. 2009, 13, 1156-1160) (280 g, 1.35 mol) and ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (Sigma-Aldrich; 303.7 g, 1.32 mol) in DMF (200 mL) at RT was treated with K2CO3 (361 g, 2.6 mol). The mixture was stirred at 80° C. in an oil bath overnight. It was cooled to RT and treated with ice water. The resulting white suspension was filtered and washed with water. The white solid was collected and dried to afford crude ethyl 4-((3-((tert-butoxycarbonyl)amino)phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate (50c) (450 g, 84% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.22 (s, 1H), 9.44 (s, 1H), 8.72 (s, 1H), 7.90 (s, 1H), 7.35-7.33 (m, 1H), 7.28-7.24 (m, 1H), 7.14-7.12 (m, 1H), 4.38-4.33 (q, 2H), 2.51 (s, 3H), 1.48 (s, 9H), 1.35 (t, 3H). m/z (ESI, +ve ion) 405.0 (M+1)−.

後処理

  1. customprepared
  2. temperatureIt was cooled to RT
  3. filtrationThe resulting white suspension was filtered
  4. washwashed with water
  5. customThe white solid was collected
  6. customdried

出典と根拠

ORDレコード
ord-bafff317481e4688820fca8e663ebf66
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346801B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート