Pyridine → HCID 86630399, compound

HRID 1091695Notes

Reaction equation

HRID 1091695 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5]([C:21]([F:24])([F:23])[F:22])=[N:6][N:7]([CH2:9][C:10]2[NH:11][C:12](=[O:20])[C:13]3[CH:18]=[C:17]([CH3:19])[S:16][C:14]=3[N:15]=2)[CH:8]=1.N1C=CC=CC=1.[S:31](Cl)([CH3:34])(=[O:33])=[O:32]>O>[CH3:34][S:31]([O:1][CH2:2][CH2:3][C:4]1[C:5]([C:21]([F:23])([F:22])[F:24])=[N:6][N:7]([CH2:9][C:10]2[NH:11][C:12](=[O:20])[C:13]3[CH:18]=[C:17]([CH3:19])[S:16][C:14]=3[N:15]=2)[CH:8]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 665916802-((4-(2-Hydroxyethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 86630399HCID 86630399, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

2-((4-(2-Hydroxyethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one (1.99 g, 5.55 mmol) was completely dissolved in pyridine (0.44 g, 20 mL, 5.55 mmol) and cooled in an acetone/sodium chloride/ice bath. Internal temperature was maintained at −10° C. Mesyl chloride (2.07 g, 1.40 mL, 18.1 mmol) was added portionwise and the temperature exothermed to 0° C. The mixture was stirred for 1 h at 0° C. and deionised water was added until solid precipitated out. The reaction was filtered, washed with water, and concentrated in vacuo to give the title compound as a pale yellow solid (2.11 g, 4.83 mmol, 87%).

Workup

  1. temperaturecooled in an acetone/sodium chloride/ice bath
  2. customexothermed to 0° C
  3. additionwas added until solid
  4. customprecipitated out
  5. filtrationThe reaction was filtered
  6. washwashed with water
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d515b2a04674d5a961109059bcc29dc
Source dataset
uspto-grants-2012_03
Patent number
US08129397B2

Reaction notes

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