Triethylamine → 4,6-Dichloro-N-(3-methoxy-5-(methylsulfonamido)phenyl)pyrimidine-5-carboxamide

HRID 1052640Notes

Reaction equation

HRID 1052640 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C(N(CC)CC)C.[Cl:22][C:23]1[C:28]([C:29](Cl)=[O:30])=[C:27]([Cl:32])[N:26]=[CH:25][N:24]=1>ClCCl>[Cl:22][C:23]1[C:28]([C:29]([NH:1][C:2]2[CH:3]=[C:4]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=2)=[O:30])=[C:27]([Cl:32])[N:26]=[CH:25][N:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chlorideHCID 68840230N-(3-amino-5-methoxyphenyl)methanesulfonamide

Product 1

HCID 901021774,6-Dichloro-N-(3-methoxy-5-(methylsulfonamido)phenyl)pyrimidine-5-carboxamideYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(3-Amino-5-methoxyphenyl)methanesulfonamide (1 g, 87% purity, 4.02 mmol) was dissolved in dichloromethane (36 ml) and triethylamine (1.35 ml, 9.65 mmol) was added. Then a solution of 4,6-dichloropyrimidine-5-carbonyl chloride (1.52 g, 67% purity, 4.82 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was added dropwise and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The crude was purified by flash chromatography (0% to 40%, hexane-ethyl acetate) using an Isolera® Purification System to give 617 mg (28% yield) of the title compound as a reddish oil. Purity 73%.

Workup

  1. washwashed with 4% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by flash chromatography (0% to 40%, hexane-ethyl acetate)
  6. customan Isolera® Purification System

Sources & evidence

ORD record
ord-58182124bb994ba9ae524b1f883aad21
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…