Sodium hydride → 2-(4-fluorophenyl)-6-morpholin-4-yl-3-(2-phenoxy-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 1581528Notes

Reaction equation

HRID 1581528 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:13][N:12]2[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:25]=2)=O)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:10])[N:11]3[CH2:15][CH:14]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[CH2:13][N:12]3[C:22]=2[C:24]2[CH:29]=[CH:28][N:27]=[C:26]([O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:25]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 121331102-(4-Fluorophenyl)-1-[4-morpholin-4-yl-2-(2-phenoxy-pyrimidine-4-carbonyl)pyrazolidine-1-yl]ethanone

Product 1

HCID 129914102-(4-fluorophenyl)-6-morpholin-4-yl-3-(2-phenoxy-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-oneYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-1-[4-morpholin-4-yl-2-(2-phenoxy-pyrimidine-4-carbonyl)pyrazolidine-1-yl]ethanone, 19, (0.2 g, 0.4 mmol) in DMF (10 mL) at 0° C. is added NaH (0.024 g, 0.6 mmol) and the resulting solution is stirred 2 hours. The solvent is removed in vacuo the residue dissolved in methylene chloride and extracted with water, dried, and re-concentrated to afford 37 mg (20% yield) of the desired product as a yellow solid.

Workup

  1. customThe solvent is removed in vacuo the residue
  2. dissolutiondissolved in methylene chloride
  3. extractionextracted with water
  4. customdried
  5. concentrationre-concentrated

Sources & evidence

ORD record
ord-dd916ceb839844e2ba068bca207e8b2c
Source dataset
uspto-grants-2004_05
Patent number
US06730668B2

Reaction notes

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