Methanesulfonyl chloride → HCID 66832667, compound

HRID 1914526Notes

Reaction equation

HRID 1914526 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH2:15]O)[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.C([N:22](C(C)C)CC)(C)C.CS(Cl)(=O)=O>C(Cl)Cl>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH2:15][NH2:22])[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66832471HCID 66832471, compound

Product 1

HCID 66832667HCID 66832667, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of [2-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-methanol (110 mg, 0.43 mmol), diisopropylethylamine (0.10 mL, 0.52 mmol), and CH2Cl2 (5 mL) was added methanesulfonyl chloride (37 μL, 0.47 mmol). After 1 h, the resulting solution was concentrated. The residue was re-dissolved in 7N NH3 in MeOH (10 mL) and heated to 70° C. in a sealed tube. After 1 h, the resulting solution was cooled, concentrated, and the residue was used crude (110 mg, 100%). MS (ESI): mass calcd. for C12H10F3N3, 253.0; m/z found, 254.1 [M+H]+.

Workup

  1. concentrationthe resulting solution was concentrated
  2. dissolutionThe residue was re-dissolved in 7N NH3 in MeOH (10 mL)
  3. waitAfter 1 h
  4. temperaturethe resulting solution was cooled
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6cc531a7a7c84fb796a963bed292f5dc
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

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