Acetic Anhydride → 4,8-bis-(2-fluoro-phenyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 556555Notes

Reaction equation

HRID 556555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([CH:14]=O)=[C:12]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[N:11]=[C:10]([S:24][CH3:25])[N:9]=1.[CH3:26][C:27](OC(C)=O)=[O:28]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]2[CH:14]=[CH:26][C:27](=[O:28])[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:12]=2[N:11]=[C:10]([S:24][CH3:25])[N:9]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 101329684-(2-Fluoro-phenyl)-6-(2-fluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Product 1

HCID 101778514,8-bis-(2-fluoro-phenyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-oneYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(2-fluoro-phenyl)-6-(2-fluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde, as described in Example 22, (400 mg, 1.1 mmol) in pyridine (2 mL) was added Ac2O (2 mL) and the reaction mixture was heated under reflux for 48 h, solvent was evaporated and the residue was dissolved in EtOAc (40 mL), washed with 1 M aq Na2CO3, and H2O and satd aq NaCl, dried (MgSO4), filtered and solvent was evaporated. The yellow residue was purified by Flash chromatography to afford pure 4,8-bis-(2-fluoro-phenyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (320 mg, 76% yield). 1H-NMR (CDCl3) δ 2.21 (s, 3H), 6.76 (d, 1H, J=9.6 Hz), 7.22-7.42 (m, 4H), 7.45-7.67 (m, 5H). LC MS (m/e)=382 (MH+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 48 h
  3. customsolvent was evaporated
  4. dissolutionthe residue was dissolved in EtOAc (40 mL)
  5. washwashed with 1 M aq Na2CO3, and H2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customsolvent was evaporated
  9. customThe yellow residue was purified by Flash chromatography

Sources & evidence

ORD record
ord-bf914d58e0304f43a8d1e2e110d5eadd
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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