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

HRID 527392
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HRID 527392 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

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온도
80 °C

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-bafff317481e4688820fca8e663ebf66
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346801B2

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