Sodium hydride → HCID 86691742, compound

HRID 1426957Notes

Reaction equation

HRID 1426957 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][O:13][C:12](=[O:15])[NH:11]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[H-].[Na+].Cl[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:21]2[N:20]=1.[NH4+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][O:13][C:12](=[O:15])[N:11]2[C:19]2[CH:24]=[CH:23][N:22]3[N:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:21]3[N:20]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 58063474Ethyl 5-chloropyrazolo(1,5-a)pyrimidine-3-carboxylateHCID 86691741(S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-one

Product 1

HCID 86691742HCID 86691742, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-4-(5-fluoro-2-methoxypyridin-3-yl)oxazolidin-2-one (254 mg, 1.20 mmol) in DMF (10 mL) was added sodium hydride (58 mg, 1.44 mmol, 60% in mineral oil). The mixture was stirred at ambient temperature for 20 minutes then treated with ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (270 mg, 1.20 mmol) in one portion. The mixture was stirred for 48 hours then treated with saturated NH4Cl solution (30 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were washed with water (5×10 mL) and brine (10 mL) then dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography, eluting with 20% EtOAc/hexanes to 66% EtOAc/hexanes, to afford (S)-ethyl 5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazo lidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (311 mg, 65% yield) as a white foam. MS (apci) m/z=401.9 (M+H).

Workup

  1. stirringThe mixture was stirred for 48 hours
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic phases were washed with water (5×10 mL) and brine (10 mL)
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 20% EtOAc/hexanes to 66% EtOAc/hexanes

Sources & evidence

ORD record
ord-ffd6d57e179349499ac056fbb60ac647
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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