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[ CAS No. 211244-82-5 ] {[proInfo.proName]}

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Product Details of [ 211244-82-5 ]

CAS No. :211244-82-5 MDL No. :MFCD12407993
Formula : C10H11N3OS Boiling Point : -
Linear Structure Formula :- InChI Key :RNYUFDKLBWLNCR-UHFFFAOYSA-N
M.W : 221.28 Pubchem ID :10560946
Synonyms :

Calculated chemistry of [ 211244-82-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.59
TPSA : 73.08 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 1.57
Log Po/w (SILICOS-IT) : 1.83
Consensus Log Po/w : 1.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.846 mg/ml ; 0.00382 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.739 mg/ml ; 0.00334 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.102 mg/ml ; 0.000462 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 211244-82-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 211244-82-5 ]

* 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 [ 211244-82-5 ]

[ 211244-82-5 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 75-03-6 ]
  • [ 211244-81-4 ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
192 mg (64%) With NaH; In N-methyl-acetamide; mineral oil; Example 21 8-Ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> To a suspension of NaH (80 mg of a 60% suspension of NaH in mineral oil) in 10 mL of dimethylformamide was added <strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (262 mg, 1.35 mmol). The reaction mixture was heated to 50 C. resulting in a brown solution. The solution was cooled slightly and iodoethane (150 muL, 1.88 mmol) was added. The reaction was heated at 50 C. for 10 minutes, then cooled to room temperature and partitioned between cold water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluding with 1:1 ethyl acetate:hexane to all ethyl acetate, to provide 192 mg (64%) of 8-ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong>, mp 104-106 C. Analysis calculated for C10H11N3OS: C, 54.28; H, 5.01; N, 18.99. Found: C, 54.28; H. 5.03; N, 19.06.
192 mg (64%) With NaH; In N-methyl-acetamide; mineral oil; Example 21 8-Ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> To a suspension of NaH (80 mg of a 60% suspension of NaH in mineral oil) in 10 mL of dimethylformamide was added <strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (262 mg, 1.35 mmol). The reaction mixture was heated to 50 C. resulting in a brown solution. The solution was cooled slightly and iodoethane (150 mL, 1.88 mmol) was added. The reaction was heated at 50 C. for 10 minutes, then cooled to room temperature and partitioned between cold water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluding with 1:1 ethyl acetate:hexane to all ethyl acetate, to provide 192 mg (64%) of 8-ethyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong>, mp 104-106 C. Analysis calculated for C10H11N3OS: C, 54.28; H, 5.01; N, 18.99. Found: C, 54.28; H, 5.03; N, 19.06.
  • 2
  • [ 211244-82-5 ]
  • [ 211244-83-6 ]
YieldReaction ConditionsOperation in experiment
93% With N-(benzenesulfonyl)-3-phenyloxaziridine In chloroform at 20℃;
  • 3
  • ethyl 3-(4-ethylamino-2-methanesulfanylpyrimidin-5-yl)acrylate [ No CAS ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
73% With 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine Heating;
  • 4
  • [ 770-31-0 ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 75 percent / tetrahydrofuran / 3 h / Heating 2.1: 45 percent / N,N-diisopropylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / Heating 3.1: NaH / dimethylformamide / 50 °C 3.2: 64 percent / dimethylformamide / 0.17 h / 50 °C
  • 5
  • [ 588-36-3 ]
  • [ 211244-82-5 ]
  • 6
  • [ 5909-24-0 ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 90 percent / Et3N / tetrahydrofuran; H2O / 0.5 h / 20 °C 2: 92 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 20 °C 3: 97 percent / MnO2 / CHCl3 / 6.5 h / 20 °C 4: 82 percent / tetrahydrofuran / 1.17 h / Heating 5: 73 percent / N,N-diisopropylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / Heating
Multi-step reaction with 6 steps 1.1: 79 percent / Et3N; aq. NH4OH / tetrahydrofuran / 2.5 h / 20 °C 2.1: 76 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C 3.1: 100 percent / MnO2 / CHCl3 / 20 °C 4.1: 75 percent / tetrahydrofuran / 3 h / Heating 5.1: 45 percent / N,N-diisopropylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / Heating 6.1: NaH / dimethylformamide / 50 °C 6.2: 64 percent / dimethylformamide / 0.17 h / 50 °C
  • 7
  • [ 776-53-4 ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 76 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C 2.1: 100 percent / MnO2 / CHCl3 / 20 °C 3.1: 75 percent / tetrahydrofuran / 3 h / Heating 4.1: 45 percent / N,N-diisopropylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / Heating 5.1: NaH / dimethylformamide / 50 °C 5.2: 64 percent / dimethylformamide / 0.17 h / 50 °C
  • 8
  • [ 185040-34-0 ]
  • [ 211244-82-5 ]
  • 9
  • [ 185040-35-1 ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / tetrahydrofuran / 1.17 h / Heating 2: 73 percent / N,N-diisopropylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / Heating
  • 10
  • [ 185040-33-9 ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 20 °C 2: 97 percent / MnO2 / CHCl3 / 6.5 h / 20 °C 3: 82 percent / tetrahydrofuran / 1.17 h / Heating 4: 73 percent / N,N-diisopropylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / Heating
  • 11
  • [ 211244-82-5 ]
  • 8-Ethyl-2-isopropylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: 20 °C
  • 12
  • [ 211244-82-5 ]
  • 8-Ethyl-2-ethylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: 20 °C
  • 13
  • [ 211244-82-5 ]
  • 2-tert-Butylamino-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: 20 °C
  • 14
  • [ 211244-82-5 ]
  • 8-ethyl-2-(methyl-phenyl-amino)-8<i>H</i>-pyrido[2,3-<i>d</i>]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 15
  • [ 211244-82-5 ]
  • 8-ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 16
  • [ 211244-82-5 ]
  • 8-Ethyl-2-(pyridin-4-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 17
  • [ 211244-82-5 ]
  • 2-Benzylamino-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 18
  • [ 211244-82-5 ]
  • [ 211245-16-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating 3: 46 percent / 48percent aq. HBr / propionic acid / 3 h / Heating
  • 19
  • [ 211244-82-5 ]
  • [ 211245-12-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 20
  • [ 211244-82-5 ]
  • 8-ethyl-2-(2-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 21
  • [ 211244-82-5 ]
  • 8-ethyl-2-(4-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 22
  • [ 211244-82-5 ]
  • 8-ethyl-2-(3-fluorophenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 23
  • [ 211244-82-5 ]
  • 2-(4-dimethylaminophenylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 24
  • [ 211244-82-5 ]
  • 2-Cyclohexylamino-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: 20 °C
  • 25
  • [ 211244-82-5 ]
  • 8-Ethyl-2-(4-pyrrol-1-yl-phenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 26
  • [ 211244-82-5 ]
  • 2-(3,4-Dimethoxy-phenylamino]-8-ethyl-8H-pyrido[2,3-d]-pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 27
  • [ 211244-82-5 ]
  • 8-ethyl-2-(4-hydroxy-3-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 28
  • [ 211244-82-5 ]
  • 8-ethyl-2-[4-(2-methoxyethoxy)phenylamino]-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating 3: 46 percent / 48percent aq. HBr / propionic acid / 3 h / Heating 4: 83 percent / K2CO3 / dimethylformamide / 0.08 h / Heating
  • 29
  • [ 211244-82-5 ]
  • 2-(4-diethylamino-phenylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 30
  • [ 211244-82-5 ]
  • 8-Ethyl-2-[3-(1,1,2,2-tetrafluoroethoxy)-phenylamino]-8H-pyrido[2,3-d]-pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 31
  • [ 211244-82-5 ]
  • 8-ethyl-2-(4-morpholin-4-yl-phenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 32
  • [ 211244-82-5 ]
  • 8-Ethyl-2-[4-(4-methylpiperazin-1-yl)-phenylamino]-8H-pyrido[2,3-d]-pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 33
  • [ 211244-82-5 ]
  • 2-[4-(2-Diethylaminoethoxy)-phenylamino]-8-ethyl-8H-pyrido[2,3-d]-pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 34
  • [ 211244-82-5 ]
  • 8-ethyl-2-(4-piperidin-1-yl-phenylamino)-8<i>H</i>-pyrido[2,3-<i>d</i>]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 35
  • [ 211244-82-5 ]
  • 8-ethyl-2-{4-[4-(3-hydroxy-propyl)-piperidin-1-yl]-phenylamino}-8<i>H</i>-pyrido[2,3-<i>d</i>]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / CHCl3 / 20 °C 2: Heating
  • 36
  • (E)-ethyl-3-(4-amino-2-(methylthio)pyrimidin-5-yl)acrylic acid [ No CAS ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 45 percent / N,N-diisopropylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / Heating 2.1: NaH / dimethylformamide / 50 °C 2.2: 64 percent / dimethylformamide / 0.17 h / 50 °C
  • 37
  • [ 113548-13-3 ]
  • [ 211244-82-5 ]
  • [ 211244-83-6 ]
YieldReaction ConditionsOperation in experiment
2.21 g (93%) In chloroform; ethyl acetate 22 8-Ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one Example 22 8-Ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of 8-ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (2.22 g, 10.04 mmol) in 100 mL of chloroform was added (+-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine (3.17 g, 12.15 mmol). The solution was stirred at room temperature overnight then concentrated in vacuo. The residue was treated with ethyl acetate to give a solid that was collected by filtration and washed with ethyl acetate to provide 2.21 g (93%) of 8-ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 202-203° C. Analysis calculated for C10H11N3O2S: C, 50.62; H, 4.67; N, 17.71. Found: C, 50.30; H, 4.54; N, 17.45.
2.21 g (93%) In chloroform; ethyl acetate 22 8-Ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one Example 22 8-Ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of 8-ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (2.22 g, 10.04 mmol) in 100 mL of chloroform was added (+-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine (3.17 g, 12.15 mmol). The solution was stirred at room temperature overnight then concentrated in vacuo. The residue was treated with ethyl acetate to give a solid that was collected by filtration and washed with ethyl acetate to provide 2.21 g (93%) of 8-ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 202-203° C. Analysis calculated for C10H11 N3O2S: C, 50.62; H, 4.67; N, 17.71. Found: C, 50.30; H, 4.54; N, 17.45.
  • 38
  • m-chloroperbenzoic acid (m-CPBA) [ No CAS ]
  • [ 211244-82-5 ]
  • [ 211244-84-7 ]
YieldReaction ConditionsOperation in experiment
147 mg (39%) In methanol; chloroform; ethyl acetate 23 8-Ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one Example 23 8-Ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of 8-ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (328 mg, 1.48 mmol) in 15 mL of chloroform was added m-chloroperbenzoic acid (m-CPBA) (810 mg of 50%-60% m-CPBA, remainder water). The reaction was stirred at room temperature for 1.5 hours then partitioned between chloroform and saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluding with a gradient of ethyl acetate to 10% methanol in ethyl acetate, to provide 147 mg (39%) of product that contained trace amounts of impurities, and 42 mg (11%) of analytically pure 8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 184-186° C. Analysis calculated for C10H11N3O3S-0.25H2O: C, 46.59; H, 4.50; N, 16.30. Found: C, 46.77; H, 4.44; N, 16.24.
147 mg (39%) In methanol; chloroform; ethyl acetate 23 8-Ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one Example 23 8-Ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of 8-ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (328 mg, 1.48 mmol) in 15 mL of chloroform was added m-chloroperbenzoic acid (m-CPBA) (810 mg of 50%-60% M-CPBA, remainder water). The reaction was stirred at room temperature for 1.5 hours then partitioned between chloroform and saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluding with a gradient of ethyl acetate to 10% methanol in ethyl acetate, to provide 147 mg (39%) of product that contained trace amounts of impurities, and 42 mg (11%) of analytically pure 8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 184-186° C. Analysis calculated for C10H11H N3O3S 0.25H2O: C, 46.59; H, 4.50; N, 16.30. Found: C, 46.77; H, 4.44; N, 16.24.
  • 39
  • [ 211244-85-8 ]
  • [ 6674-22-2 ]
  • [ 211244-82-5 ]
YieldReaction ConditionsOperation in experiment
1.83 g (33%) In N-ethyl-N,N-diisopropylamine O.21 8-Ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one Alternate Preparation of Example 21 8-Ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of ethyl 3-(4-ethylamino-2-methanesulfanyl-pyrimidin-5-yl)acrylate (6.62 g, 24.78 mmol) in 30 mL of N,N-diisopropylethylamine was added 4.25 mL of 1,8-diazabicyclo[5.4.0]undec-7ene. The reaction mixture was heated at reflux overnight then cooled to room temperature. The resultant solid was collected by filtration and washed with 1:1 hexane:ethyl acetate to give 1.83 g (33%) of 8-ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one. The filtrate was concentrated in vacuo and upon the addition of hexane, a solid formed that was collected, washed with hexane, and purified by flash chromatography eluding with ethyl acetate to provide an additional 2.22 g (40%) of title product.
1.83 g (33%) In N-ethyl-N,N-diisopropylamine O.21 8-Ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one Alternate Preparation of Example 21 8-Ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of ethyl 3-(4-ethylamino-2-methanesulfanyl-pyrimidin-5-yl)acrylate (6.62 g, 24.78 mmol) in 30 mL of N,N-diisopropylethylamine was added 4.25 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was heated at reflux overnight then cooled to room temperature. The resultant solid was collected by filtration and washed with 1:1 hexane:ethyl acetate to give 1.83 g (33%) of 8-ethyl-2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one. The filtrate was concentrated in vacuo and upon the addition of hexane, a solid formed that was collected, washed with hexane, and purified by flash chromatography eluding with ethyl acetate to provide an additional 2.22 g (40%) of title product.
YieldReaction ConditionsOperation in experiment
65% With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere; Sealed tube; 15 Preparation 15 (0758) 8-benzyl-2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-7(8H)-one [(XI), R2 = benzyl, R3 = R4 = R5= H] step 3a’ General procedure: A mixture of 2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-7(8H)-one (100 mg, 0.52 mmol), cesium carbonate (337 mg, 1.04 mmol), and benzyl bromide (133 mg, 0.78 mmol) in anhydrous DMF (2 mL) was purged with nitrogen and heated in a sealed tube at 90 °C for 1 h. The reaction mixture was allowed to cool to room temperature and diluted with water. The product precipitated, filtered and washed with water. To afford 8-benzyl-2-(methylsulfanyl)pyrido[2,3- d]pyrimidin-7(8H)-one as a yellow solid (117 mg, 80% yield). (0760) 1H NMR (500 MHz, DMSO- cfe) d = 8.91 (s, 1 H), 8.00 (d, J = 9.46 Hz, 1 H), 7.17 - 7.35 (m, 5H), 6.71 (d, J = 9.46 Hz, 1 H), 5.50 (s, 2H), 2.50 (s, 3H). LCMS : m/z 284 [M+H]+ r.t. 5.92 min. HRMS (ESI) calcd for C15H14N3OS [M + H]+ 284.0852 found 284.0865
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere; Sealed tube; Preparation 5 2-(methylsulfanyl)-8-(propan-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one [(XII), U = Y = CH, X = N, , R2 = propan-2-yl, R3 = H] step 3g General procedure: A mixture of 2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-7(8H)-one (100 mg, 0.52 mmol), cesium carbonate (337 mg, 1.04 mmol), and isopropyl iodide (77.8 ul, 0.78 mmol) in anhydrous DMF (2 mL) was purged with nitrogen and heated in a sealed tube at 70 °C for 2h. The reaction mixture was allowed to cool to room temperature and diluted with water. The product precipitated, filtered and washed with water. To give the title compound as a light yellow solid (86 mg, 70% yield).1H NMR (401 MHz, DMSO-d6) δ = 8.85 (s, 1H), 7.87 (d, J = 9.52 Hz, 1H), 6.57 (d, J = 9.40 Hz, 1H), 5.69 (td, J = 6.93, 13.73 Hz, 1H), 2.60 (s, 3H), 1.54 (d, J = 6.96 Hz, 6H). LCMS: m/z 236 [M+H]+ r.t.5.53 min. HRMS (ESI) calcd for C11H14N3OS [M + H]+ 236.0852 found 236.0861.
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