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

HRID 1375414Notes

Reaction equation

HRID 1375414 reaction equation
[NH2:1][C:2]1[C:3]([NH:23][CH3:24])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Cl:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30]([Cl:39])[C:31]=1[C:32](=O)[C:33]([O:35]CC)=O.CC(O)=O>COCCO>[Cl:39][C:30]1[CH:29]=[N:28][CH:27]=[C:26]([Cl:25])[C:31]=1[C:32]1[C:33](=[O:35])[N:23]([CH3:24])[C:3]2[N:4]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:11][CH:10]=3)[N:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 587867785-Amino-2-[[4-[2-(diethylamino)ethoxy]phenyl]amino]-4-(methylamino)pyrimidineHCID 58786793Ethyl 2-(3,5-dichloropyridin-4-yl)-2-oxoacetate

Product 1

HCID 99144306-(3,5-Dichloropyridin-4-yl)-8-methyl-2-[[4-[2-(diethylamino)ethoxy]-phenyl]amino]-8H-pteridin-7-oneYield 15.3%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 0.465 g (1.4 mmol) of 5-amino-2-[[4-[2-(diethylamino)-ethoxy]-phenyl]amino]-4-(methylamino)pyrimidine, 0.69 g (2.8 mmol) of ethyl 2-(3,5-dichloropyridin-4-yl)-2-oxoacetate, and 0.5 mL of HOAc in 15 mL of 2-methoxyethanol is heated under reflux for 18 hours, and the reaction is worked up as above in 6 to give 0.11 g (15%) of the title compound (Compound 20): mp (MeOH) 179–180.5° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 hours

Sources & evidence

ORD record
ord-b44cbaf3951149a3b37481e114a83899
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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