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[ CAS No. 76872-23-6 ] {[proInfo.proName]}

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Product Details of [ 76872-23-6 ]

CAS No. :76872-23-6 MDL No. :MFCD15144570
Formula : C7H4Cl2N2S Boiling Point : -
Linear Structure Formula :- InChI Key :BTGNDWIMNVJZJY-UHFFFAOYSA-N
M.W : 219.09 Pubchem ID :11106847
Synonyms :

Safety of [ 76872-23-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 76872-23-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 76872-23-6 ]

[ 76872-23-6 ] Synthesis Path-Downstream   1~33

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  • [ 76872-45-2 ]
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  • [ 76872-71-4 ]
  • [ 76872-23-6 ]
YieldReaction ConditionsOperation in experiment
74% b) 2, 4-dichloro-6-methylthieno[2, 3-dJpyrimidine; According to Scheme 10 Step 2: 6-methylthieno[2,3-d]pyrimidine-2,4(lH,5H)-dione (0.89Og, 0.488mmol) was added by portion into phosphorous oxychloride (5.92ml, 63.5mmol) for 20min. The mixture was stirred at r.t for 10 minutes, then pyridine (9.77mmol) was added dropwise for 5min. The mixture was then heated at 110C for 45min. The excess of phosphorous oxychloride was removed in vacuo and the residue was taken up in dichloromethane and quickly washed with cold water. The organic phase was dried over MgSO4, filtered, and evaporated till dryness, yielding crude title compound as a brown solid, (0.79Og, 74%).
21% With N,N-dimethyl-aniline; trichlorophosphate; at 80℃; for 12h; j00374j A mixture of compound B-50 (2.0 g, 11 mmol) and dimethylaniline (1.9 g, 16 mmol) in phosphorus oxychloride (272 mL) was stirred at 80 C for 12 hours. On completion, the mixture was concentrated, poured into water (40 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic phase was washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 5:11 to give compound B-51 (0.50 g, 21% yield) as a yellow solid. LCMS (J): tR=1.221 mi, (ES+) mlz (M+H)+ 241.2
With trichlorophosphate; at 150℃; for 3h; EXAMPLE 16 2,4-Dichloro-6-methylthieno[2,3-d]pyrimidine; 6-Methylthieno[2,3-d]pyrimidine-2,4(1 H,3H)-dione (Example 10, 2.0 g) and POCI3 were heated together in a sealed tube at 150 0C for 3 hours. The mixture was then cooled and concentrated under reduced pressure and the residue was partitioned between dichlorom ethane and aqueous saturated sodium bicarbonate. The organic layer was dried over MgSO4, filtered and concentrated. The residue was triturated with diethyl ether containing a small amount of acetonitrile and the resulting solid was collected and dried under reduced pressure to give the title compound (1.75 g). MS (ESI+) m/z219.05 (M+H)+.
With 2,3-Dimethylaniline; trichlorophosphate; at 140℃; for 12h; Example 8b: 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine; [0326] Example 8a (500mg, 2.75mmol, leq) was dissolved in Phosphorus oxychloride (200ml) containing l%v/v of Dimethylaniline in a high pressure reaction vessel. The solution was heated to 14O0C for 12 hours. Product was confirmed by LCMS. The phosphorus oxychloride was removed in vacuo and the residue co-evaporated with toluene (3x100ml) to leave 1.03g of approximately 60% pure product, which was used without further purification. [M+H] calc'd for C7H4CL2N2S, 219; found, 219.

  • 4
  • [ 31230-17-8 ]
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  • [ 952147-16-9 ]
YieldReaction ConditionsOperation in experiment
64% In N,N-dimethyl-formamide; at 50℃; for 4h; Example 8c: 2-chloro-6-methyl-N-(5-methyl-lH-pyrazol-3-yl)thieno[2,3-d]pyrimidin-4- amine; [0327] Example 8b (approx 60% pure, Ig, 2.74mmol, leq) was reacted with 5- methyl-lH-pyrazol-3 -amine (797mg, 8.22mmol, 3eq)was stirred in DMF (20ml) at 5O0C <n="117"/>for 4 hours. The reaction was complete by LCMS. Addition of water (200ml) caused the title product to appear as a tan solid, which was collected by filtration. (498mg, 64%). [M+H] calc'd for Ci6Hi5N7S, 338; found, 338.
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  • [ 79041-61-5 ]
  • 10
  • [ 76872-23-6 ]
  • 7-Methyl-1,5-dihydro-imidazo[1,2-a]thieno[2,3-d]pyrimidin-2-one [ No CAS ]
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  • [ 76872-23-6 ]
  • 6-Chloro-7-methyl-1,5-dihydro-imidazo[1,2-a]thieno[2,3-d]pyrimidin-2-one [ No CAS ]
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  • [ 79603-56-8 ]
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  • [ 79603-57-9 ]
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  • [ 2620-50-0 ]
  • [ 76872-23-6 ]
  • [ 203564-66-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; EXAMPLE 1 3.02 g of 3,4-methylenedioxybenzylamine ("A") are added to a solution of 3.29 g of <strong>[76872-23-6]2,4-dichloro-6-methylthieno[2,3-d]pyrimidine</strong> in 80 ml of dichloro-methane, and, after 1.52 g of triethylamine have been added, the mixture is stirred for 12 hours at room temperature. The solvent is removed and worked up as customary. This gives 3.38 g of 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 162.
With triethylamine; In dichloromethane; EXAMPLE 1 3.02 g of 3,4-methylenedioxybenzylamine ("A") are added to a solution of 3.29 g of 2,4-dichloro-6-methylthieno-[2,3-d]-pyrimidine in 80 ml of methylene chloride and, after addition of 1.52 g of triethylamine, the mixture is stirred at room temperature for 12 hours. The solvent is removed and the residue is worked up in the customary manner. 3.38 g of 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine are obtained, m.p. 162.
With triethylamine; In dichloromethane; EXAMPLE 1 2-Chloro-6-Methyl-4-(3,4-Methylenedioxybenzylamino)-Thieno-[2,3-d]-Pyrimidine A solution of 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine (3.29 g) in dichloromethane (30 ml) is charged with 3,4-methylenedioxybenzylamine ("A") (3.02 g). Triethylamine (1.52 g) is added, and the mixture is stirred at room temperature. The solvent is removed, and the usual workup yields 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine (3.38 g) Mp. 162 C.
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  • [ 76872-23-6 ]
  • [ 5188-07-8 ]
  • 2-chloro-6-methyl-4-(methylthio)thieno[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; water; for 4h;Heating / reflux; To a THE (50 mL) solution of <strong>[76872-23-6]2,4-dichloro-6-methylthieno[2,3-d]pyrimidine</strong> (3.80 g, 17.3 mmol) was added a 15% aqueous sodium methyl mercaptan solution (9.71 g, 20.8 mmol), followed by heating under reflux for 4 hours. After completion of the reaction, the precipitated salt was filtrated off and the filtrate was poured into water and extracted with ethyl acetate. The resulting extract solution was washed with water and brine and then the solvent was removed by evaporation. A part of the product was purified on a silica gel column (Kiesel gel 60 manufactured by MERCK, 20% AcOEt-Hex) to obtain 2-chloro-6-methyl-4-(methylthio)thieno[2,3-d]pyrimidine. The remainder was used in the next reaction without purification. 1H-NMR (400MHz, CDCl3): 2.60(d, 3H, J=1.2Hz), 2.70(s, 3H), 6.94(q, 1H, J=1.2Hz). mp: 111-112C
  • 17
  • 2,4-dihydroxy-6-methylthieno[2,3-d]pyrimidine [ No CAS ]
  • [ 76872-23-6 ]
YieldReaction ConditionsOperation in experiment
79% With trichlorophosphate; In DMF (N,N-dimethyl-formamide); at 100℃; for 2.5h;Heating / reflux; Phosphorus oxychloride (28.1 g, 0.184 mol) was added to a DMF (10 mL) solution of 2,4-dihydroxy-6-methylthieno[2,3-d]pyrimidine (6.70 g, 36.8 mmol), followed by heating under reflux at 100C for 2.5 hours. After completion of the reaction, the reaction liquid was poured into ice-water and precipitated crystals were collected by filtration. After the resulting crystals were dissolved in ethyl acetate, the solution was washed with water and brine and then the solvent was removed by evaporation to obtain 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine (6.40 g, 79%). 1H-NMR (400MHz, CDCl3): 2.65(d, 3H, J=1.2Hz), 7.07(q, 1H, J=1.2Hz). mp: 145-146C
  • 18
  • [ 76872-23-6 ]
  • biphenyl-4-yl(piperazin-1-yl)methanone [ No CAS ]
  • [ 902766-03-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; EXAMPLE 44 4-[4-(1 ,1 '-Biphenyl-4-ylcarbonyl)piperazin-1 -yl]-2-chloro-6-methylthieno[2,3-d]pyrimidine; 2,4-Dichloro-6-methylthieno[2,3-d]pyrimidine (Example 16, 0.80 g) was dissolved in a mixture of THF/DMF (10 mL/6 mL) followed by addition of 1-(1 ,1'-biphenyl-4-ylcarbonyl)piperazine (1.45 g, 3.65 mmol) and diisopropylethylamine (0.61 g, 4.7 mmol). The mixture was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and brine. The organic layer was separated and washed additional four times with brine. The organic layer was dried over MgSO4, filtered and concentrated. The resulting residue was stirred in hot acetonitrile with a few drops of methanol. The resulting solid was collected and dried under reduced pressure to give 1.41 g of the title compound. MS (ESI+) for C24H21CIN4OS1 m/z 449.242 (M+H)+. 1H NMR (400 MHz, CDCI3) δ 7.66 to 7.36 (m, 9H), 6.93 (s, 1H), 3.95 (br s, 8H), 2.54 (s, 3H).
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  • [ 76872-23-6 ]
  • [ 140-75-0 ]
  • 2-chloro-6-methyl-4-(4-fluorobenzylamino)-thieno-[2,3-d]-pyrimidine [ No CAS ]
  • 2-chloro-5-methyl-4-(4-fluorobenzylamino)-thieno-[2,3-d]-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 45 Following the procedure of Example 1, the reaction of 4-fluorobenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(4-fluorobenzylamino)-thieno-[2,3-d]-pyrimidine with 2,4-dichloro-5-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-5-methyl-4-(4-fluorobenzylamino)-thieno-[2,3-d]-pyrimidine.
  • 20
  • [ 76872-23-6 ]
  • [ 100-46-9 ]
  • 2-chloro-6-methyl-4-benzylamino-thieno-[2,3-d]-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 34 Following the procedure of Example 1, the reaction of benzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-benzylamino-thieno-[2,3-d]-pyrimidine.
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  • [ 115514-77-7 ]
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  • 2-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)-thieno-[2,3-d]-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 12 Following the procedure of Example 1, the reaction of 3-chloro-4-methoxybenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)-thieno-[2,3-d]-pyrimidine.
EXAMPLE 12 Following the procedure of Example 1, the reaction of 3-chloro-4-methoxybenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)-thieno-[2,3-d]-pyrimidine
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  • [ 7409-18-9 ]
  • [ 76872-23-6 ]
  • 2-chloro-6-methyl-4-(3-nitrobenzylamino)-thieno-[2,3-d]-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 66 Following the procedure of Example 1, the reaction of 3-nitrobenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3-nitrobenzylamino)-thieno-[2,3-d]-pyrimidine.
EXAMPLE 66 Following the procedure of Example 1, the reaction of 3-nitrobenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3-nitrobenzylamino)-thieno-[2,3-d]-pyrimidine
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  • [ 76872-23-6 ]
  • [ 5763-61-1 ]
  • 2-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)-thieno-[2,3-d]-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 23 Following the procedure of Example 1, the reaction of 3,4-dimethoxybenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)-thieno-[2,3-d]-pyrimidine.
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  • [ 76872-23-6 ]
  • [ 102-49-8 ]
  • 2-chloro-6-methyl-4-(3,4-dichlorobenzylamino)-thieno-[2,3-d]-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 55 Following the procedure of Example 1, the reaction of 3,4-dichlorobenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3,4-dichlorobenzylamino)-thieno-[2,3-d]-pyrimidine.
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  • [ 1484-85-1 ]
  • [ 76872-23-6 ]
  • 2-chloro-6-methyl-4-(3-nitrobenzylamino)-thieno-[2,3-d]-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 77 Following the procedure of Example 1, the reaction of 3,4-methylenedioxyphenethylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3-nitrobenzylamino)-thieno-[2,3-d]-pyrimidine.
EXAMPLE 77 Following the procedure of Example 1, the reaction of 3,4-methylenedioxyphenethylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3-nitrobenzylamino)-thieno-[2,3-d]-pyrimidine
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  • [ 76872-23-6 ]
  • [ 64-04-0 ]
  • 2-chloro-6-methyl-N-phenethylthieno[2,3-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92.7% With potassium carbonate; In acetonitrile; at 80℃; for 17h; c) 2-chloro-6-methyl-N-phenethylthieno[2,3-d]pyrimidin-4-amine; According to Scheme 10 Step 3: A suspension of 2,4-dichloro-6-methylthieno[2,3-d] pyrimidine (0.70Og, 3.20mmol), phenethylamine (0.481ml, 3.83mmol) and potassium carbonate (0.662g, 4.79mmol) in acetonitrile (6ml) was heated at 80C to 17 hours. Then, a little of water was added to the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over MgSO4, filtered, and evaporated till dryness. The residue (brown solid, 1.0Og) was purified by chromatography over silica gel (Flashmart Pack: 50g/60-40um, eluent DCM) yielding title compound (0.90Og, 92.7%) as a yellow solid..
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  • [ 1607479-53-7 ]
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  • [ 76872-23-6 ]
  • [ 1607479-54-8 ]
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  • [ 138564-58-6 ]
  • [ 503-38-8 ]
  • [ 76872-23-6 ]
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  • [ 19369-53-0 ]
  • [ 76872-23-6 ]
  • 32
  • [ 76872-23-6 ]
  • 2-chloro-6-methylthieno[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With ammonium hydroxide; zinc; In ethanol; at 80℃; for 3h; j00376j A mixture of compound B-51 (0.45 g, 2.1 mmol), zinc (1.1 g, 16 mmol) and aqueous ammonia (0.40 mL, 10 mmol, 27%) in ethanol (5.0 mL) was stirred at 80 C for 3 hours. On completion, the mixture was filtered, concentrated in vacuo, dissolved in water (40 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic phase was washed with brine (30 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 10:11 to give compound B-52 (0.16 g, 42% yield) as a yellow solid. ‘H-NMR (CDC13, 400 MHz): 8.82 (s, 1H), 6.98 (d, J1.2 Hz, 1H), 2.64 (s, 3H).
  • 33
  • [ 76872-23-6 ]
  • (R)-N-(6-methylthieno[2,3-d]pyrimidin-2-yl)-4H-1‘-azaspiro[isoxazole-5,3'-bicyclo[2.2.2]octan]-3-amine hydrochloride [ No CAS ]
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