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

HRID 1640230Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-854083aabbf745f58b3fbeac6616ac38
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110575B2

Reaction notes

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