Dimethylformamide → N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]benzamide

HRID 243541Notes

Reaction equation

HRID 243541 reaction equation
CN(C)C=O.[CH3:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([CH3:16])[C:14]=1[OH:15])[C:10]#[N:11].[Br:17][C:18]1[C:19]([NH:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:20][C:21]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)=[N:22][C:23]=1Cl>O>[Br:17][C:18]1[C:19]([NH:34][C:35](=[O:42])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[N:20][C:21]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)=[N:22][C:23]=1[O:15][C:14]1[C:13]([CH3:16])=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[CH3:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 71465003N-[5-bromo-6-chloro-2-(4-cyanophenylamino)-pyrimidin-4-yl]benzamide

Product 1

HCID 70978955N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1000 ml of dimethylformamide, 51.52 g of 3,5-dimethyl-4-hydroxybenzonitrile, 106.9 g of diazabicyclo undecene were added to a reaction vessel and stirred at RT. The reaction mixture was maintained at same temperature for 1 hr and 100 g of N-[5-bromo-6-chloro-2-(4-cyanophenylamino)-pyrimidin-4-yl]benzamide added with continued stirring for 30 mins. The reaction mixture was heated to 100-110° C. and further maintained at same temperature for 24 hr. After completion of the reaction, the reaction mixture was cooled to RT and 2000 ml of water added and stirred at RT for 1 hr. The reaction mixture was filtered. The obtained solid was dried under vacuum (0.5 kg/cm2) at 55-60° C. overnight.

Workup

  1. temperatureThe reaction mixture was maintained at same temperature for 1 hr
  2. stirringwith continued stirring for 30 mins
  3. temperatureThe reaction mixture was heated to 100-110° C.
  4. temperaturefurther maintained at same temperature for 24 hr
  5. customAfter completion of the reaction
  6. temperaturethe reaction mixture was cooled to RT
  7. stirringstirred at RT for 1 hr
  8. filtrationThe reaction mixture was filtered
  9. customThe obtained solid was dried under vacuum (0.5 kg/cm2) at 55-60° C. overnight

Sources & evidence

ORD record
ord-6a8b4db4b0cd406994b1427c1e79748c
Source dataset
uspto-grants-2014_02
Patent number
US08653266B2

Reaction notes

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