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

HRID 1375413Notes

Reaction equation

HRID 1375413 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.[Br:23][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([Br:37])[C:29]=1[C:30](=O)[C:31]([O:33]CC)=O.CC(O)=O>COCCO.CCOC(C)=O>[Br:37][C:28]1[CH:27]=[N:26][CH:25]=[C:24]([Br: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

6

Reactant 3

HCID 176Acetic AcidHCID 587867813,5-Dibromo-alpha-oxo-4-pyridineaceticacidethylesterHCID 587868125-Amino-4-(methylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidine

Product 1

HCID 99597986-(3,5-Dibromopyridin-4-yl)-8-methyl-2-[[4-(morpholin-4-yl)phenyl]amino]-8H-pteridin-7-oneYield 26.2%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0–30 g (1 mmol) of 5-amino-4-(methylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidine, 0.67 g (2 mmol) of ethyl 2-(3,5-dibromopyridin-4-yl)-2-oxoacetate (from preparation 17), and 0.5 mL of HOAc in 15 mL of 2-methoxyethanol is heated under reflux for 18 hours. Workup in EtOAc, followed by chromatography on silica, eluting with CH2Cl2/EtOAc (4:1), gives 0.15 g (26%) of the title compound (Compound 19): mp (EtOH) 204–206° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 hours
  3. washeluting with CH2Cl2/EtOAc (4:1)

Sources & evidence

ORD record
ord-6675fa2b7abd410e805f9804b5ce69b3
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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