Sodium Hydroxide → 2-(4-Fluorophenyl)-1-[4-methoxy-2-(2-methylsulfanyl-pyrimidine-4-carbonyl)pyrazolidine-1-yl]-ethanone

HRID 1061634Notes

Reaction equation

HRID 1061634 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([O:16][CH3:17])[CH2:13][NH:12]2)=[O:10])=[CH:4][CH:3]=1.[CH3:18][S:19]([C:22]1[N:27]=[C:26]([C:28](Cl)=[O:29])[CH:25]=[CH:24][N:23]=1)(=O)=O.[OH-].[Na+]>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([O:16][CH3:17])[CH2:13][N:12]2[C:28]([C:26]2[CH:25]=[CH:24][N:23]=[C:22]([S:19][CH3:18])[N:27]=2)=[O:29])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 219921912-(4-Fluorophenyl)-1-(4-methoxy-pyrazolidin-1-yl)-ethanoneHCID 219921942-Methylsulfonyl-pyrimidine-4-carbonyl chloride

Product 1

HCID 219921822-(4-Fluorophenyl)-1-[4-methoxy-2-(2-methylsulfanyl-pyrimidine-4-carbonyl)pyrazolidine-1-yl]-ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-(4-Fluorophenyl)-1-(4-methoxy-pyrazolidin-1-yl)-ethanone, 47, (7.67 g, 32.2 mmol) and 2-methylsulfonyl-pyrimidine-4-carbonyl chloride (9.11 g, 48.3 mmol) are dissolved in dichloromethane (150 mL). A 0.5 N aqueous solution of sodium hydroxide (150 mL) is added steadily via addition funnel and the mixture is stirred vigorously at room temperature for 4 hours. The reaction is diluted with 5% aqueous sodium carbonate solution (1 L). The mixture is extracted with dichloromethane (6×200 mL). The combined organic layers are dried over magnesium sulfate, filtered and concentrated to give a red oil. The crude material is purified by over silica (1:1 to 1:3 hexane/ethyl acetate to 100% ethyl acetate) to afford 10.3 g of the desired product as a brown, viscous oil.

Workup

  1. extractionThe mixture is extracted with dichloromethane (6×200 mL)
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a red oil
  6. customThe crude material is purified by over silica (1:1 to 1:3 hexane/ethyl acetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-caa5a6d7ffe74d479029873264bd1763
Source dataset
uspto-grants-2005_11
Patent number
US06960593B2

Reaction notes

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