Cyclohexene → 9-Ethyl-4-[(1-methylpiperidin-4-yl)methylamino]imidazo[5,1-h]pteridin-6(5H)-one

HRID 377510

Reaction equation

HRID 377510 reaction equation
ClC1C([N+]([O-])=[O:9])=C(Cl)N=CN=1.[CH3:12][N:13]1[CH2:18][CH2:17][CH:16](NC)[CH2:15][CH2:14]1.[CH2:21]([C:23]1[NH:24][CH:25]=[CH:26][N:27]=1)[CH3:22].C1CCCCC=1.[C:34]([N:41]1[CH:45]=[CH:44][N:43]=[CH:42]1)([N:36]1C=[CH:39][N:38]=[CH:37]1)=O>[Pd].C(O)C>[CH2:21]([C:23]1[N:27]2[C:26]([C:42](=[O:9])[NH:43][C:44]3[C:37]([NH:38][CH2:39][CH:16]4[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]4)=[N:36][CH:34]=[N:41][C:45]=32)=[CH:25][N:24]=1)[CH3:22]

Participants

8

Reactant 5

HCID 8079CyclohexeneHCID 203124,6-Dichloro-5-nitropyrimidineHCID 661302-EthylimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 5663231-Methyl-4-(methylamino)piperidine

Product 1

HCID 702709349-Ethyl-4-[(1-methylpiperidin-4-yl)methylamino]imidazo[5,1-h]pteridin-6(5H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Prepared by treatment of 4,6-dichloro-5-nitropyrimidine with 1-methyl-4-(methylamino)piperidine followed by reaction with 2-ethylimidazole, reduction with palladium on carbon and cyclohexene in refluxing ethanol, and cyclization with carbonyidiimidazole.

Sources & evidence

ORD record
ord-3212f7b590b4430483b6c6024c3e6bfd
Source dataset
uspto-grants-2000_02
Patent number
US06025489

Linked notes

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