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Potassium Carbonate → 1-[4-Chloro-6-(4-methoxybenzyl)amino-{1,3,5}-triazin-2-yl-amino]-imidazolidine-2,4-dione

HRID 76340
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HRID 76340 반응식
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][N:10]2[CH2:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[CH:27][CH:26]=1>CC#N>[Cl:8][C:6]1[N:7]=[C:2]([NH:32][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[N:3]=[C:4]([NH:9][N:10]2[CH2:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[N:5]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 866980651-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]imidazolidine-2,4-dione

생성물 1

HCID 866980691-[4-Chloro-6-(4-methoxybenzyl)amino-{1,3,5}-triazin-2-yl-amino]-imidazolidine-2,4-dione수율 66%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 1-(4,6-dichloro-[1,3,5]-triazin-2-yl-amino)-imidazolidine-2,4-dione (Example 1.1, Part A) (3.84 g, 14.6 mmol) and K2CO3 (4.4 g, 31.8 mmol) in CH3CN (50 mL) was added (4-methoxyphenyl)-methanamine (2.0 g, 14.6 mmol) drop-wise at 0° C. The mixture was stirred at r.t. overnight. TLC showed the reaction was complete. The mixture was filtered and the cake was portioned between water and EtOAc. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give the expected compound (3.50 g, yield: 66%) as a white solid. It was used for the next step without further purification. δH (400 MHz, DMSO-d6): 11.30-11.23 (m, 1H), 10.06-9.83 (m, 1H), 8.67-8.60 (m, 1H), 7.24-7.13 (m, 2H), 6.90-6.83 (m, 2H), 4.40-4.35 (m, 2H), 4.26-4.05 (m, 2H), 3.73 (s, 3H). Mass spectrum (ESI) m/z 364 (100%, MH+).

후처리

  1. filtrationThe mixture was filtered
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1eac722e09f5458a85089d0914b7739c
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835629B2

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