Triethylamine → HCID 16064930, compound

HRID 1160057Notes

Reaction equation

HRID 1160057 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=CC=3)=[N:8][C:7]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:6][C:5]=2[S:4][C:3]=1[CH3:30].[CH2:31]([N:33](CC)CC)C.Cl.[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45](Cl)=[O:46]>>[CH3:1][C:2]1[C:10]2[C:9]([NH:11][C:12]3[CH:31]=[N:33][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:16][CH:17]=3)=[N:8][C:7]([N:24]3[CH2:25][CH2:26][N:27]([C:45]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][N:39]=4)=[O:46])[CH2:28][CH2:29]3)=[N:6][C:5]=2[S:4][C:3]=1[CH3:30]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 68420321HCID 68420321, compound

Product 1

HCID 16064930HCID 16064930, compoundYield 35%

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 226.40 mg (1.26 mmol) of 6-morpholinopyridin-3-amine and 130.90 mg (1.23 mmol) of calcium carbonate, 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 440 mg (quantitative) of 2-chloro-5,6-dimethyl-N-(6-morpholinopyridin-3-yl)-thenio[2,3-d]pyrimidine-4-amine. 200 mg (0.50 mmol) of the obtained product was dissolved in 20 ml of 1-butanol in a sealed tube, and 220 μl (1.50 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 25 mg (12% yield) of 5,6-dimethyl-N-(6-morpholinopyridin-3-yl)-2-(piperazin-1-yl)thieno[2,3-d]pyrimidine-4-amine. To 9 mg (0.02 mmol) of the obtained compound, 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 crystallized from ethyl acetate, thus obtaining 7 mg (35% yield) of the title product.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solvent, dimethyl chloride, was evaporated under reduced pressure
  3. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c6491b480e742a896955b1c5dbe4361
Source dataset
uspto-grants-2010_10
Patent number
US07816351B2

Reaction notes

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