Pyridinium chloride → HCID 178510036, compound

HRID 589556Notes

Reaction equation

HRID 589556 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[N:11]=1>C(#N)C>[OH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[N:11]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 522706964-(4-Methoxypyrimidin-2-ylamino)benzonitrile

Product 1

HCID 178510036HCID 178510036, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
155 °C

Procedure

Pyridine hydrochloride (23 gm) was added to 4-(4-methoxypyrimidin-2-ylamino)benzonitrile (15 gm) and then heated to 150 to 160° C. for 3 hours. The mixture was then cooled to room temperature, then transferred into ice water and stirred for 1 hour. The resulting precipitate was filtered and washed with water. The solid thus obtained was slurried in acetonitrile at 0 to 5° C. for 1 hour and filtered. The solid obtained was dried to give 12.3 gm of 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customThe solid thus obtained
  5. filtrationfiltered
  6. customThe solid obtained
  7. customwas dried

Sources & evidence

ORD record
ord-10e8430065534a009f3f2b144d3f4582
Source dataset
uspto-grants-2016_01
Patent number
US09233935B2

Reaction notes

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