Diisopropylethylamine → Ethyl 6-(3-methyl-2,5-dioxo-1',3'-dihydrospiro[imidazolidin-4,2'-inden]-5'-ylamino)pyrimidine-4-carboxylate

HRID 1640230노트

반응식

HRID 1640230 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[N:11]1[CH3:17])[CH2:5]2.CCN(C(C)C)C(C)C.Cl[C:28]1[N:33]=[CH:32][N:31]=[C:30]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:29]=1>CN(C=O)C.O>[CH3:17][N:11]1[C:6]2([CH2:5][C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:28]4[N:33]=[CH:32][N:31]=[C:30]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:29]=4)[CH:3]=3)[CH2:7]2)[C:14](=[O:15])[NH:13][C:12]1=[O:16]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 18440306(-)-5'-Amino-3-methyl-spiro[imidazolidine-4,2'-indane]-2,5-dioneHCID 22756838Ethyl 6-chloropyrimidine-4-carboxylate

생성물 1

HCID 58117486Ethyl 6-(3-methyl-2,5-dioxo-1',3'-dihydrospiro[imidazolidin-4,2'-inden]-5'-ylamino)pyrimidine-4-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

500 mg (2.16 mmol) 5′-amino-3-methyl-1′,3′-dihydrospiro[imidazolidine-4,2′-indene]-2,5-dione (Bioorg. Med. Chem. Lett.; 2006; 16; 24; 6165-6169) and 400 μL (2.33 mmol) DIPEA were added to 400 mg (2.14 mmol) ethyl 6-chloropyrimidine-4-carboxylate in 10 mL DMF and the reaction mixture was stirred for 8 h at 100° C. The reaction mixture was diluted with 60 mL water and stirred for 30 min. The precipitate was suction filtered and the filtrate was extracted with dichloromethane (3×40 mL). The organic phases were combined, dried on magnesium sulphate, filtered and evaporated down i.vac. The residue was dissolved in DMF and purified by preparative HPLC. The product fractions were combined and freeze-dried.

후처리

  1. stirringstirred for 30 min
  2. filtrationfiltered
  3. extractionthe filtrate was extracted with dichloromethane (3×40 mL)
  4. customdried on magnesium sulphate
  5. filtrationfiltered
  6. customevaporated down i.vac
  7. dissolutionThe residue was dissolved in DMF
  8. custompurified by preparative HPLC
  9. customfreeze-dried

출처 및 근거

ORD 기록
ord-854083aabbf745f58b3fbeac6616ac38
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110575B2

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