Diethyl Ether → 2-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]acetic acid

HRID 3227

Reaction equation

HRID 3227 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:13]2[N:14]=[C:15]([NH2:18])[N:16]=[CH:17][C:12]=2[CH:11]=[C:10]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[C:9]1=[O:27])(C)(C)C.FC(F)(F)C(O)=O.C(OCC)C>C(Cl)Cl>[NH2:18][C:15]1[N:16]=[CH:17][C:12]2[CH:11]=[C:10]([C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[C:9](=[O:27])[N:8]([CH2:7][C:6]([OH:28])=[O:5])[C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 5328630tert-butyl 2-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]acetate

Product 1

HCID 53286312-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]acetic acidYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid tert-butyl ester (157 mg, 0.37 mmol) from Example 36 in 4 mL of methylene chloride was added 2 mL of trifluoroacetic acid. The solution was stirred at room temperature for 5 hours, then concentrated in vacuo. The resultant oil was partitioned between methylene chloride and brine. The aqueous layer was washed with ethyl acetate, and the organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give a gummy solid. Diethyl ether was added, and the resultant precipitate was collected. Hexane was added to the filtrate, and once again the resultant precipitate was collected. The solids were combined and dried in vacuo at 80° C. to give 71 mg (52%) of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid that was >97% pure by HPLC; mp 297°-300° C. dec.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant oil was partitioned between methylene chloride and brine
  3. washThe aqueous layer was washed with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a gummy solid
  8. customthe resultant precipitate was collected
  9. additionHexane was added to the filtrate
  10. customonce again the resultant precipitate was collected
  11. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-abec610d41fa4460bcec11b0f48f849d
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

Loading…