4-Toluenesulfonyl chloride → HCID 20819940, compound

HRID 496013Notes

Reaction equation

HRID 496013 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:8][C:6]2[CH:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[N:3]=[C:2]([NH2:1])[N:7]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1354185802-Amino-4-hydroxy-6-(trifluoromethyl)pyrimidine

Product 1

HCID 20819940HCID 20819940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-6-(trifluoromethyl)-4(3H)-pyrimidinone (250 mg, 1.4 mmol), triethylamine (196 μL, 1.4 mmol), N,N-dimethylaminopyridine (17 mg, 0.14 mmol), in CH2Cl2 (13 mL) cooled to 0° C. was added p-toluenesulfonyl chloride (534 mg, 2.8 mmol). The mixture was stirred at room temperature for 16 h. The mixture was diluted with CH2Cl2, washed with H2O (2×20 mL) followed by brine, dried (Na2SO4), evaporated, and dried under vacuum. Desired compound (466 mg, 1.4 mmol; 99+% yield; ES MS [M+H]+=140.

Workup

  1. washwashed with H2O (2×20 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-599b8c4ee10d458eb5bc3624f5a10bed
Source dataset
uspto-grants-2005_09
Patent number
US06943172B2

Reaction notes

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