4,6-Dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidine → 5-isopropyl-N-[6-chloro-5-(p-tolyl)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide

HRID 2085086Notes

Reaction equation

HRID 2085086 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:3]=1.[K+].[CH:23]([C:26]1[CH:27]=[CH:28][C:29]([S:32]([NH-:35])(=[O:34])=[O:33])=[N:30][CH:31]=1)([CH3:25])[CH3:24]>CN(C=O)C>[CH:23]([C:26]1[CH:27]=[CH:28][C:29]([S:32]([NH:35][C:2]2[C:7]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)=[C:6]([Cl:15])[N:5]=[C:4]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[N:3]=2)(=[O:34])=[O:33])=[N:30][CH:31]=1)([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 219795754,6-Dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidineHCID 1317209445-Isopropyl pyridine-2-sulfonamide potassium salt

Product 1

HCID 227294005-isopropyl-N-[6-chloro-5-(p-tolyl)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamideYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 654 mg of 4,6-dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidine and 1051 mg of 5-isopropyl-2-pyridine sulfonamide potassium salt (Example 1e) in 20 ml of DMF was stirred for 16 h at room temperature. Eventually, the solvent was distilled off under reduced pressure and the resulting residue was treated with 100 ml of 10% aqueous acetic acid and 100 ml of DCM. The layers were separated. The aqueous layer was extracted two more times with DCM. The combined organic layers were washed once with water, dried over MgSO4 and evaporated. The remaining residue was crystallised from isopropanol:diethyl ether. The yellow crystals were collected, washed with cold isopropanol and diethyl ether, and dried under high vacuum to furnish 870 mg of 5-isopropyl-N-[6-chloro-5-(p-tolyl)-2-(4-pyridyl)4-pyrimidinyl]-2-pyridine sulfonamide. LC-MS: tR=5.06 min, [M+1]+=480.40, [M−1]−=478.48.

Workup

  1. distillationEventually, the solvent was distilled off under reduced pressure
  2. additionthe resulting residue was treated with 100 ml of 10% aqueous acetic acid and 100 ml of DCM
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted two more times with DCM
  5. washThe combined organic layers were washed once with water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe remaining residue was crystallised from isopropanol
  9. customThe yellow crystals were collected
  10. washwashed with cold isopropanol and diethyl ether
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-92ea178dc51344079a945b5a7de97aa5
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

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