Triethylamine → Methanesulfonic acid 2-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-ethyl ester

HRID 403488Notes

Reaction equation

HRID 403488 reaction equation
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].[CH3:25][S:26](Cl)(=[O:28])=[O:27].CCN(CC)CC>>[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:19][CH2:20][CH2:21][O:22][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:23][CH:24]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 683794832-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-ethanol

Product 1

HCID 86671752Methanesulfonic acid 2-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-ethyl ester

Procedure

A mixture of 2-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-ethanol (10) (200 mg, 0.62 mmol), methanesulfonyl chloride (0.05 ml, 0.62 mmol) and Et3N (0.09 ml, 0.62 mmol) was stirred at room temperature for 2 h. Then the reaction was quenched by addition of CH2Cl2 and water. The organic layer was then extracted with water and NaCl-solution, dried over Na2 SO4 and evaporated. The crude product was used in the next step without purification.

Workup

  1. customThen the reaction was quenched by addition of CH2Cl2 and water
  2. extractionThe organic layer was then extracted with water and NaCl-solution
  3. customdried over Na2 SO4
  4. customevaporated
  5. customThe crude product was used in the next step without purification

Sources & evidence

ORD record
ord-b0323163defe44a99204cba07a3a8913
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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