Potassium Fluoride → 4-[6-ethynyl-2-(2-fluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

HRID 1398689Notes

Reaction equation

HRID 1398689 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=2)[C:8]2[CH:17]=[C:18]([C:21]#[C:22][Si](C)(C)C)[CH:19]=[CH:20][C:7]=2[N:6]=1.[F-].[K+]>CO>[C:21]([C:18]1[CH:19]=[CH:20][C:7]2[N:6]=[C:5]([O:4][CH2:3][CH2:2][F:1])[N:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[C:8]=2[CH:17]=1)#[CH:22]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 866696144-[2-(2-fluoroethoxy)-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 866696154-[6-ethynyl-2-(2-fluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amineYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[2-(2-fluoroethoxy)-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (100 mg, 0.27 mmol) and potassium fluoride (64 mg, 0.68 mmol) in methanol (3 mL) was stirred at 50° C. for 3 hr. The reaction mixture was concentrated under vacuum and the residue was diluted with 30 mL of ethyl acetate. The resulting mixture was washed with 3×10 mL of water and the organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 70 mg (87%) of 4-[6-ethynyl-2-(2-fluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a yellow solid: LC-MS: m/z=+298 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthe residue was diluted with 30 mL of ethyl acetate
  3. washThe resulting mixture was washed with 3×10 mL of water
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d254d534df374520bc657532c120e1ab
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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