Triethylamine → HCID 16064789, compound

HRID 1160056Notes

Reaction equation

HRID 1160056 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)=[CH:14][CH:13]=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].C(N(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:17]=[CH:16][C:15]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)=[CH:14][CH:13]=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 16064789HCID 16064789, compoundYield 30%

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. customAfter completion of the reaction
  2. customthe reaction solvent, dimethyl chloride, was evaporated under reduced pressure
  3. customthe residue was crystallized from dimethyl chloride

Sources & evidence

ORD record
ord-e7082b9cbae947d997642c5047b429b8
Source dataset
uspto-grants-2010_10
Patent number
US07816351B2

Reaction notes

Loading…