Water → HCID 59639621, compound

HRID 2357264Notes

Reaction equation

HRID 2357264 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:30].O.CCOCC.C[N:38]1CCCC1=O>>[NH2:38][C:16]1[N:17]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C:13]2[CH:12]=[CH:11][C:10](=[O:30])[N:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[C:14]=2[N:15]=1

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 13387N-methyl-2-pyrrolidoneHCID 10296381HCID 10296381, compound

Product 1

HCID 59639621HCID 59639621, compoundYield 53%

Procedure

To a solution of 8-(2,6-difluoro-phenyl)-4-(2-fluoro-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one (432 mg, 1 mmol) in 1-methyl-2-pyrrolidinone (5 mL) was added NaNH2 (195 mg, 5 mmol, 5 eq) and the mixture was heated to 50°. After 1 h, H2O (20 mL) was added then Et2O (20 mL). The layers were separated. The organic layer was washed with satd aq NaCl, dried (MgSO4), filtered and solvent was removed in vacuo. The yellow residue was then purified by Flash chromatography to afford 2-amino-8-(2,6-difluoro-phenyl)-4-(2-fluoro-phenyl)-8H-pyrido[2,3-d]pyrimidin-7-one (100 mg, 53% yield). 1H-NMR (CDCl3) δ 5.51 (br s, 2H), 6.42 (d, 1H, J=9.8 Hz), 7.08 (m, 2H), 7.30 (m, 2H), 7.50 (m, 4H), LC MS (m/e)=369 (MH+). Rt=1.77 min.

Workup

  1. temperaturethe mixture was heated to 50°
  2. customThe layers were separated
  3. washThe organic layer was washed with satd aq NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customsolvent was removed in vacuo
  7. customThe yellow residue was then purified by Flash chromatography

Sources & evidence

ORD record
ord-9ea7b2857e1a47098283f4c624bc5067
Source dataset
uspto-grants-2010_07
Patent number
US07759486B2

Reaction notes

Loading…