Ammonium Hydroxide → HCID 66776385, compound

HRID 1616098Notes

Reaction equation

HRID 1616098 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][C:10]([F:13])([F:12])[F:11])[N:3]=1.[NH4+:14].[OH-]>CC#N>[F:11][C:10]([F:13])([F:12])[CH2:9][S:8][C:4]1[N:3]=[C:2]([NH2:14])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86662548HCID 86662548, compound

Product 1

HCID 66776385HCID 66776385, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To solution of 4-chloro-2-(2,2,2-trifluoro-ethylsulfanyl)-pyrimidine (22 g, 0.096 mol) in 350 mL of CH3CN was added NH4OH (400 mL). The mixture was stirred for 24 hours at 90° C. in a sealed tube. The mixture was then cooled to room temperature and the solvent was concentrated in vacuo, the residue was extracted with ethyl acetate, dried over MgSO4 and the crude was purified by column chromatography on silica gel to give 2-(2,2,2-trifluoro-ethylsulfanyl)-pyrimidin-4-ylamine (14.3 g, 71.3%) as a white solid.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationthe solvent was concentrated in vacuo
  3. extractionthe residue was extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. customthe crude was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b1c3bb6750da4a359111610dffa6e1ea
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

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