Aniline → HCID 87445249, compound

HRID 1160055Notes

Reaction equation

HRID 1160055 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=2[N:7]=1.[CH2:14]1[N:19]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[CH2:18][CH2:17][O:16][CH2:15]1.NC1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:26][C:23]2[CH:22]=[CH:21][C:20]([N:19]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:25][CH:24]=2)[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 3645909HCID 3645909, compound

Product 1

HCID 87445249HCID 87445249, compoundYield 112.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 240 mg (1.02 mmol of 2,4-dichloro-5,6-dimethyl-thieno[2,3-d]pyrimidine in 50 ml of ethyl alcohol were added 220.20 mg (1.23 mmol) of 4-(4-morpholino)aniline and 130.90 mg (1.23 mmol) of aniline, and then the mixture was stirred under reflux. After completion of the reaction, the reaction solvent, ethyl alcohol, was evaporated under reduced pressure, and the residue was crystallized from ethyl alcohol and filtered, yielding 430 mg (quantitative) of 2-chloro-5,6-dimethyl-thieno[2,3-d]pyrimidin-4-yl-4-morpholin-4-yl-phenylamine. 220 mg (0.53 mmol) of the obtained product was dissolved in 20 ml of 1-butanol in a sealed tube, and 223 μl (1.59 mmol) of triethylamine and 45.9 mg of piperazine were added thereto, and the mixture was stirred at 120° C. After completion of the reaction, the resulting solid was filtered and the filtrate was concentrated under reduced pressure and then crystallized from ethyl acetate, yielding 30 mg (15% yield) of 5,6-dimethyl-2-piperazin-1-yl-thieno[2,3-d]pyrimidin-4-yl-4-morpholin-4-yl-phenylamine. To 9 mg (0.02 mmol) of the obtained compound and 5,6-dimethyl-2-piperazin-1-yl-thieno[2,3-d]pyrimidin-4-yl-4-morpholin-4-yl-phenylamine in 5 ml of dimethyl chloride were added 3.5 μl (0.02 mmol) of triethylamine and 4.1 mg (0.02 mmol) of picolinoyl chloride hydrochloride, and then the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solvent, dimethyl chloride, was evaporated under reduced pressure, and the residue was crystallized from dimethyl chloride, thus obtaining 6 mg (30% yield) of the title product.

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. customthe reaction solvent, ethyl alcohol, was evaporated under reduced pressure
  4. customthe residue was crystallized from ethyl alcohol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3815cc67bc134a9ea7fd66692f6e64fb
Source dataset
uspto-grants-2010_10
Patent number
US07816351B2

Reaction notes

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