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

HRID 1375410Notes

Reaction equation

HRID 1375410 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:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[C:31](=O)[C:32]([O:34]CC)=O.CC(O)=O>COCCO>[Cl:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([Cl:23])[C:25]=1[C:31]1[C:32](=[O:34])[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 587868125-Amino-4-(methylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidineHCID 69476762Ethyl 2-(2,6-dichlorophenyl)-2-oxoacetate

Product 1

HCID 98914386-(2,6-Dichlorophenyl)-8-methyl-2-[[4-(morpholin-4-yl)phenyl]amino]-8H-pteridin-7-oneYield 37.2%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 0.60 g (2 mmol) of 5-amino-4-(methylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidine, 0.74 g (3 mmol) ethyl 2-(2,6-dichlorophenyl)-2-oxoacetate (T. H. Kress and M. R. Leanna, Synthesis, 1988:803–805), and 0.3 mL HOAc in 25 mL of 2-methoxyethanol is heated under reflux for 16 hours before the solvent is removed under vacuum. The residue is extracted into EtOAc and, after being washed with water, the solution is dried over Na2SO4. Removal of the solvent and chromatography on silica, eluting with hexane/EtOAc 3:2 gives 0.36 g (37%) of the title compound (Compound 2 in Tables 1 and 2): mp (EtOH) 292–293° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours before the solvent
  3. customis removed under vacuum
  4. extractionThe residue is extracted into EtOAc
  5. washafter being washed with water
  6. dry with materialthe solution is dried over Na2SO4
  7. customRemoval of the solvent and chromatography on silica
  8. washeluting with hexane/EtOAc 3:2

Sources & evidence

ORD record
ord-10431ca12a404182ae47cd931decd0de
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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