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

HRID 1375411Notes

Reaction equation

HRID 1375411 reaction equation
[NH2:1][C:2]1[C:3]([NH:21][CH3:22])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Cl:23][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([Cl:37])[C:29]=1[C:30](=O)[C:31]([O:33]CC)=O.CC(O)=O>COCCO>[Cl:37][C:28]1[CH:27]=[N:26][CH:25]=[C:24]([Cl:23])[C:29]=1[C:30]1[C:31](=[O:33])[N:21]([CH3:22])[C:3]2[N:4]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:11][CH:10]=3)[N:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 58786793Ethyl 2-(3,5-dichloropyridin-4-yl)-2-oxoacetateHCID 587868125-Amino-4-(methylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidine

Product 1

HCID 98699396-(3,5-Dichloropyridin-4-yl)-8-methyl-2-[[4-(morpholin-4-yl)phenyl]amino]-8H-pteridin-7-oneYield 18%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 0.30 g (1 mmol) of 5-amino-4-(methylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidine, 0.37 g (1.5 mmol) of ethyl 2-(3,5-dichloropyridin-4-yl)-2-oxoacetate, and 0.3 mL HOAc in 15 mL 2-methoxyethanol as heated under reflux for 16 hours, and worked up as above in 2. Chromatography on alumina, eluting with CH2Cl2/EtOAc (4:1), gives 85 mg (18%) of the title compound (Compound 12 in Tables 1 and 2): mp (MeOH) 243–245° C.

Workup

  1. temperatureas heated
  2. temperatureunder reflux for 16 hours
  3. washChromatography on alumina, eluting with CH2Cl2/EtOAc (4:1)

Sources & evidence

ORD record
ord-a5c059358bc24b5397f7683946e3b79d
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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