Pyridine → HCID 67071276, compound

HRID 1260241Notes

Reaction equation

HRID 1260241 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][CH:6]([C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][N:10]=2)[CH2:5]1)[CH2:2][CH3:3].N1C=CC=CC=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.CC[O-].[Na+]>C(Cl)Cl.CCO>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:15][C:12]2[CH:11]=[N:10][C:9]([CH:6]3[CH2:7][CH2:8][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5]3)=[N:14][CH:13]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 2723922Sodium ethoxideHCID 57494447HCID 57494447, compound

Product 1

HCID 67071276HCID 67071276, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The crude 2-(1-propyl-pyrrolidin-3-yl)-pyrimidin-5-ylamine (about 1.11 mmol) was dissolved in CH2Cl2:pyridine, 9:1 (50 ml) and 4-bromobenzensulfonyl chloride (566 mg, 2.21 mmol) was added. After stirring at room temperature overnight, the reaction mixture was filtered and concentrated. The raw material was then dissolved in a solution of EtONa (400 mg, 5.87 mmol) in EtOH (35 ml) and the resulting solution was heated under reflux for 1 h. Silica gel (1 g) was next added to the mixture and the solvent removed under reduced pressure. Following flash column chromatography (CH2Cl2:methanol, 9:1) provides the title compound (100 mg, 21% for four steps) as a yellow gum.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. temperaturethe resulting solution was heated
  4. temperatureunder reflux for 1 h
  5. additionSilica gel (1 g) was next added to the mixture
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-267244b143fc47d190b8214d22fbac8c
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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