Acetic Acid → 6-(3,5-Dichloropyridin-4yl)-2-[[4-(diethylaminocarbonyl)phenyl]-amino]-8-methyl-8H-pteridin-7-one

HRID 1375416Notes

Reaction equation

HRID 1375416 reaction equation
[NH2:1][C:2]1[C:3]([NH:22][CH3:23])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Cl:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([Cl:38])[C:30]=1[C:31](=O)[C:32]([O:34]CC)=O.CC(O)=O>COCCO.CCOC(C)=O>[Cl:38][C:29]1[CH:28]=[N:27][CH:26]=[C:25]([Cl:24])[C:30]=1[C:31]1[C:32](=[O:34])[N:22]([CH3:23])[C:3]2[N:4]=[C:5]([NH:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])=[CH:13][CH:14]=3)[N:6]=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 587867825-Amino-2-[[4-(diethylaminocarbonyl)phenyl]amino]-4-(methylamino)pyrimidineHCID 58786793Ethyl 2-(3,5-dichloropyridin-4-yl)-2-oxoacetate

Product 1

HCID 98059046-(3,5-Dichloropyridin-4yl)-2-[[4-(diethylaminocarbonyl)phenyl]-amino]-8-methyl-8H-pteridin-7-oneYield 28%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.50 g (1.6 mmol) of 5-amino-2-[[4-(diethylaminocarbonyl)-phenyl]amino]-4-(methylamino)pyrimidine, 0.8 g (3.2 mmol) of ethyl 2-(3,5-dichloropyridin-4-yl)-2-oxoacetate, and 0.5 mL of HOAc in 20 mL of 2-methoxyethanol is heated under reflux for 16 hours. Workup in EtOAc, followed by chromatography on silica, eluting with EtOAc/hexane (3:2), gives 0.22 g (28%) of the title compound (Compound 13): mp (i-Pr2O) 230–231° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours
  3. washeluting with EtOAc/hexane (3:2)

Sources & evidence

ORD record
ord-03160d11e74a47fbb36fd15acbeae84b
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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