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

HRID 1640230ノート

反応式

HRID 1640230 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-854083aabbf745f58b3fbeac6616ac38
出典データセット
uspto-grants-2012_02
特許番号
US08110575B2

反応ノート

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