Ammonia → GE-0012

HRID 1908950Notes

Reaction equation

HRID 1908950 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:5]=[C:4]([O:17][C:18]2[C:25]([CH3:26])=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=2[CH3:27])[CH:3]=1.O1CCOCC1.O.[NH3:35]>C1(C)C=CC=CC=1>[NH2:35][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:5]=[C:4]([O:17][C:18]2[C:25]([CH3:26])=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=2[CH3:27])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 312751,4-DioxaneHCID 509149464-{[6-Chloro-2-(4-cyanoanilino)pyrimidin-4-yl]oxy}-3,5-dimethylbenzonitrile

Product 1

HCID 486367GE-0012

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

4-[[6-chloro-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-benzonitrile (24 gm) was dissolved in aqueous ammonia (240 ml) and 1,4-dioxane (274 ml) at room temperature. The contents were heated to 120° C. and maintained for 12 hours at 120° C. To the reaction mass was added water (360 ml) and the reaction mass was slowly cooled to 50 to 60° C. The reaction mass was further cooled to 0 to 5° C. and stirred for 1 hour at 0 to 5° C., filtered. The wet solid obtained was dissolved in toluene (150 ml) under stirring. The separated solid was filtered and dried at 50° C. to obtain 10 gm of 4-[[6-amino-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile.

Workup

  1. customat room temperature
  2. temperaturemaintained for 12 hours at 120° C
  3. temperaturethe reaction mass was slowly cooled to 50 to 60° C
  4. temperatureThe reaction mass was further cooled to 0 to 5° C.
  5. filtrationfiltered
  6. customThe wet solid obtained
  7. stirringunder stirring
  8. filtrationThe separated solid was filtered
  9. customdried at 50° C.

Sources & evidence

ORD record
ord-1233d621d41b4be39f24cb0aa144ddf3
Source dataset
uspto-grants-2013_12
Patent number
US08598341B2

Reaction notes

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