Triethylamine → HCID 90102725, compound

HRID 1052545Notes

Reaction equation

HRID 1052545 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.C(N(CC)CC)C.[Cl:21][C:22]1[C:27]([C:28](Cl)=[O:29])=[C:26]([Cl:31])[N:25]=[CH:24][N:23]=1>O1CCCC1.ClCCl>[Cl:21][C:22]1[C:27]([C:28]([O:8][C:6]2[CH:5]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=[C:2]([OH:1])[CH:7]=2)=[O:29])=[C:26]([Cl:31])[N:25]=[CH:24][N:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chlorideHCID 90102924HCID 90102924, compound

Product 1

HCID 90102725HCID 90102725, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(3,5-Dihydroxyphenyl)methanesulfonamide (260 mg, 1.28 mmol) was dissolved in tetrahydrofuran (5 ml) and triethylamine (214 μl, 1.52 mmol) was added. Then a solution of 4,6-dichloropyrimidine-5-carbonyl chloride (298 mg, 1.40 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dropwise added. The reaction mixture was stirred at room temperature over 48 hours. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The product was purified by reverse phase using SP1® Purification System to give 280 mg (18% yield) of the title compound. Purity 100%.

Workup

  1. washwashed with 4% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified by reverse phase
  6. custom® Purification System

Sources & evidence

ORD record
ord-4be03dc77fe540d2b69dd514f559635d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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