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[ CAS No. 104680-25-3 ] {[proInfo.proName]}

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Chemical Structure| 104680-25-3
Chemical Structure| 104680-25-3
Structure of 104680-25-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 104680-25-3 ]

CAS No. :104680-25-3 MDL No. :MFCD08059079
Formula : C10H13NO4S Boiling Point : -
Linear Structure Formula :- InChI Key :PUNYRKPPRGWNOC-UHFFFAOYSA-N
M.W : 243.28 Pubchem ID :5282562
Synonyms :

Calculated chemistry of [ 104680-25-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.9
TPSA : 106.86 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) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 1.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.59
Solubility : 0.618 mg/ml ; 0.00254 mol/l
Class : Soluble
Log S (Ali) : -4.12
Solubility : 0.0185 mg/ml ; 0.0000759 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.28
Solubility : 1.29 mg/ml ; 0.00528 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 104680-25-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 104680-25-3 ]

* 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 [ 104680-25-3 ]

[ 104680-25-3 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 104680-25-3 ]
  • [ 80691-81-2 ]
  • [ 104680-24-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; tin(ll) chloride; sodium nitrite 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min; Yield given. Multistep reaction;
  • 2
  • [ 104680-25-3 ]
  • [ 91619-41-9 ]
  • Ethyl 3-[3-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: bis(trichloromethyl) carbonate; 2-amine-thiophene-3,4-dicarboxylic acid ethyl ester With triethylamine In tetrahydrofuran; dichloromethane at 0℃; for 1h; Stage #2: 3-[1-(1,2,3,4-tetrahydro)quinolinyl]sulfonylaniline In tetrahydrofuran; dichloromethane at 20℃; Stage #3: With sodium ethanolate In ethanol at 60℃; for 2h; 32 Ethyl 3-[3-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate Example 32 Ethyl 3-[3-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate To a solution of diethyl 2-aminothiophene-3,4-dicarboxylate (100 mg), triethylamine (0.21 ml) in dichloromethane (3 ml), a solution of triphosgene (44.5 mg) in THF (1 ml) was added at 0°C, and the mixture was stirred under nitrogen atmosphere at 0°C for 1 hr. The insoluble material was removed by filtration. 3-(3,4-Dihydroquinolin-1(2H)-ylsulfonyl)aniline (118 mg) was added, and the mixture was stirred under nitrogen atmosphere at room temperature overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography, and dissolved in ethanol (7 ml). A 20% solution (140 mg) of sodium ethoxide in ethanol was added, and the mixture was stirred under nitrogen atmosphere at 60°C for 2 hr. After allowing to cool to room temperature, water-saturated brine was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, and crystallized from diisopropyl ether to give the object (69.7 mg) as crystals. 1H-NMR (DMSO-d6) δ 1.23 (3H, t), 1.58-1.69 (2H, m), 2.43-2.54 (2H, m), 3.72-3.79 (2H, m), 4.21 (2H, q), 7.04-7.10 (2H, m), 7.12-7.22 (1H, m), 7.47-7.63 (5H, m), 7.73 (1H, s), 12.46 (1H, s).
  • 3
  • [ 104680-25-3 ]
  • [ 104635-64-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature 3: 92 percent / 1 N sodium hydroxide / ethanol / 1 h / Ambient temperature 4: 43 percent / chlorine / CHCl3; CCl4 / 0.67 h / 10 - 15 °C 5: 74 percent / 1 N aq. sodium hydroxide / methanol / 1.5 h / 60 °C
  • 4
  • [ 104680-25-3 ]
  • [ 104650-06-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature 3: 92 percent / 1 N sodium hydroxide / ethanol / 1 h / Ambient temperature
  • 5
  • [ 104680-25-3 ]
  • [ 104679-90-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature 3: 92 percent / 1 N sodium hydroxide / ethanol / 1 h / Ambient temperature 4: 43 percent / chlorine / CHCl3; CCl4 / 0.67 h / 10 - 15 °C
  • 6
  • [ 104680-25-3 ]
  • [ 114652-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature
  • 7
  • [ 104680-25-3 ]
  • [ 259862-14-1 ]
YieldReaction ConditionsOperation in experiment
With sodium borohydrid; sodium hydrogencarbonate In water; cyclopropanecarboxylic acid 44.a a a Diethyl 2-[(cyclopropylmethyl)amino]-3,4-thiophenedicarboxylate Sodium borohydride (12.5 g) was added portionwise over 3 hours to a solution of diethyl 2-amino-3,4-thiophenedicarboxylate (25 g) in cyclopropanecarboxylic acid (125 ml). After a further 18 hours, further sodium borohydride (5 g) was added and the mixture heated at 50° C. for 18 hours. Further sodium borohydride (5 g) was added and the mixture stirred at 50° C. for 16 hours then at room temperature for 3 days. Water (500 ml) was added, the solution made alkaline by addition of sodium bicarbonate and extracted with ether (2*250 ml). Organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluding with ether/isohexane (2:3) to give the sub-title compound (12.1 g) as an oil. MS (+ve APCI) 298 ((M+H)+)
  • 8
  • [ 104680-25-3 ]
  • [ 1423165-49-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: water; sodium hydroxide / methanol / 3 h / Reflux 4.1: triethylamine; diphenyl phosphoryl azide 4.2: 0.42 h / 125 °C / Microwave irradiation
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: sodium hydroxide; water / methanol / 3 h / Reflux 4.1: diphenyl phosphoryl azide; triethylamine / tetrahydrofuran 4.2: 0.42 h / 125 °C / Microwave irradiation
  • 9
  • [ 104680-25-3 ]
  • [ 1423165-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C
Multi-step reaction with 2 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C
  • 10
  • [ 104680-25-3 ]
  • [ 1423165-52-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C
  • 11
  • [ 104680-25-3 ]
  • [ 1423165-53-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C
  • 12
  • [ 104680-25-3 ]
  • [ 1423165-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C
  • 13
  • [ 104680-25-3 ]
  • [ 1423166-94-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C
  • 14
  • [ 104680-25-3 ]
  • [ 1423165-55-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C
  • 15
  • [ 104680-25-3 ]
  • [ 1423162-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C
  • 16
  • [ 104680-25-3 ]
  • [ 1423162-68-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C
Multi-step reaction with 2 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C
  • 17
  • [ 104680-25-3 ]
  • [ 1423162-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane
  • 18
  • [ 104680-25-3 ]
  • [ 1423162-75-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / tetrahydrofuran; N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5: trifluoroacetic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C
  • 19
  • [ 104680-25-3 ]
  • [ 1423162-76-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / 20 °C
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C
  • 20
  • [ 104680-25-3 ]
  • [ 1423162-77-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5: ammonia; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water; N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ammonia; 4-(4-benzylpiperazin-1-yl)thieno[2,3-d]pyrimidin-2-amine / water; N,N-dimethyl-formamide / 20 °C
  • 21
  • [ 104680-25-3 ]
  • [ 1423163-26-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: water; sodium hydroxide / methanol / 3 h / Reflux 4.1: methanol; sodium tetrahydroborate / tetrahydrofuran 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C 5.2: 20 °C
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: sodium hydroxide; water / methanol / 3 h / Reflux 4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 1 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C 5.2: 20 °C
  • 22
  • [ 104680-25-3 ]
  • [ 1423163-27-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: water; sodium hydroxide / methanol / 3 h / Reflux 4.1: triethylamine; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 20 h / 20 °C 4.2: 1 h / 150 °C / Microwave irradiation 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 5.2: 20 °C
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: sodium hydroxide; water / methanol / 3 h / Reflux 4.1: triethylamine / N,N-dimethyl-formamide / 20 h / 20 °C 4.2: 1 h / 150 °C / Microwave irradiation 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 5.2: 20 °C
  • 23
  • [ 104680-25-3 ]
  • [ 1423163-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
  • 24
  • [ 104680-25-3 ]
  • [ 1423163-45-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
  • 25
  • [ 104680-25-3 ]
  • [ 1423163-48-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
  • 26
  • [ 104680-25-3 ]
  • [ 1423163-73-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: triethylamine / dichloromethane / 12 h / 20 °C
  • 27
  • [ 104680-25-3 ]
  • [ 1423163-99-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: triethylamine / methanol / 0.5 h / 20 °C 3.2: 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: triethylamine / methanol / 0.5 h / 20 °C 3.2: 2 h / 0 - 20 °C
  • 28
  • [ 104680-25-3 ]
  • [ 1423165-09-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 3 h
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 3 h
  • 29
  • [ 104680-25-3 ]
  • [ 1423165-10-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 2 h / 20 °C
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 2 h / 20 °C
  • 30
  • [ 104680-25-3 ]
  • [ 1423165-11-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C 6.1: potassium <i>tert</i>-butylate / dichloromethane / 2 h / 20 °C
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C 6.1: potassium <i>tert</i>-butylate / dichloromethane / 2 h / 20 °C
  • 31
  • [ 104680-25-3 ]
  • C19H25N5O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: water; sodium hydroxide / methanol / 3 h / Reflux 4: triethylamine / tetrahydrofuran / 1 h / 20 °C
  • 32
  • [ 104680-25-3 ]
  • [ 1423165-32-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C
Multi-step reaction with 2 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C
  • 33
  • [ 104680-25-3 ]
  • [ 1423165-33-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: water; sodium hydroxide / methanol / 3 h / Reflux
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: sodium hydroxide; water / methanol / 3 h / Reflux
  • 34
  • [ 104680-25-3 ]
  • [ 1423165-34-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: water; sodium hydroxide / methanol / 3 h / Reflux 4: methanol; sodium tetrahydroborate / tetrahydrofuran
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: sodium hydroxide; water / methanol / 3 h / Reflux 4: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 1 h / 20 °C
  • 35
  • [ 104680-25-3 ]
  • [ 1423165-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: water; sodium hydroxide / methanol / 3 h / Reflux 4.1: triethylamine; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 20 h / 20 °C 4.2: 1 h / 150 °C / Microwave irradiation
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: sodium hydroxide; water / methanol / 3 h / Reflux 4.1: triethylamine / N,N-dimethyl-formamide / 20 h / 20 °C 4.2: 1 h / 150 °C / Microwave irradiation
  • 36
  • [ 104680-25-3 ]
  • [ 1423165-46-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: water; sodium hydroxide / methanol / 3 h / Reflux 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; ammonium chloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 12 h
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: sodium hydroxide; water / methanol / 3 h / Reflux 4: ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine / N,N-dimethyl-formamide / 12 h
  • 37
  • [ 104680-25-3 ]
  • [ 1423165-47-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: water; sodium hydroxide / methanol / 3 h / Reflux 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; ammonium chloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 12 h 5: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 12.5 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: sodium hydroxide; water / methanol / 3 h / Reflux 4: ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine / N,N-dimethyl-formamide / 12 h 5: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 12.5 h / 0 - 20 °C
  • 38
  • carbamimidic chloride hydrochloride [ No CAS ]
  • [ 104680-25-3 ]
  • [ 1423165-17-6 ]
YieldReaction ConditionsOperation in experiment
781 mg With dimethylsulfone at 135℃; for 0.75h; 13 2-Amino-5 -(ethoxycarbonyl)thieno [2,3 -dlpyrimidin-4( 111)-one INTERMEDIATE 132-Amino-5-(ethoxycarbonyl)thieno[2,3-(i pyrimidin-4(lH)-oneA mixture of Intermediate 12 (1.0 g, 4.1 mmol), chloroformamidine hydrochloride (1.181 g, 10.3 mmol) and dimethylsulfone (1.932 g, 20.5 mmol) was heated at 135°C for 45 minutes. Water was added and the mixture was cooled down to room temperature. An aqueous ammonia solution was added to adjust the solution to pH 9. The precipitate was filtered off, yielding the title compound (781 mg) as a white powder. 13C NMR δ (75 MHz, CDC13) 169.24, 163.33, 157.02, 153.90, 129.29, 120.85, 112.43, 60.73, 14.15. MS (m/z) 240 [M+H]+.
781 mg With dimethylsulfone at 135℃; for 0.75h; 2-Amino-5-(ethoxycarbonyl)thieno[2,3-d]pyrimidin-4(1H)-one 0272] A mixture of Intermediate 12 (1.0 g, 4.1 mmol), chloroformamidine hydrochloride (1.181 g, 10.3 mmol) and dimethylsulfone (1.932 g, 20.5 mmol) was heated at 135° C. for 45 minutes. Water was added and the mixture was cooled down to room temperature. [0273] An aqueous ammonia solution was added to adjust the solution to pH 9. The precipitate was filtered off, yielding the title compound (781 mg) as a white powder. 13C NMR δ (75 MHz, CDCl3) 169.24, 163.33, 157.02, 153.90, 129.29, 120.85, 112.43, 60.73, 14.15. MS (m/z) 240 [M+H]+.
  • 39
  • [ 617-35-6 ]
  • [ 105-56-6 ]
  • [ 104680-25-3 ]
YieldReaction ConditionsOperation in experiment
1.828 g With sulfur; triethylamine In N,N-dimethyl-formamide at 65℃; for 5h; 12 Diethyl 2-aminothiophene-3 ,4-dicarboxylate INTERMEDIATE 12Diethyl 2-aminothiophene-3 ,4-dicarboxylateTo a solution of ethyl pyruvate (1.778 mL, 16 mmol), ethyl cyanoacetate (2.388 mL, 22.4 mmol) and triethylamine (2.669 mL, 19.2 mmol) in N,N-dimethylformamide (8.0 mL) was added sulfur (564 mg, 17.6 mmol; finely ground using a mortar). The suspension was heated at 60°C for 5 hours. The solvents were removed in vacuo and the slurry was dissolved in ethyl acetate. The organic solution was extracted successively with brine, saturated aqueous sodium bicarbonate solution, brine, hydrogen chloride (IN) and again brine. The organic fraction was dried over magnesium sulfate after which the solvent was removed in vacuo. The crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of heptane and ethyl acetate (in a ratio gradually ranging from 20% to 30% ethyl acetate in heptane), yielding the title compound (1.828 g) as a yellow powder. 13C NMR δ (75 MHz, CDC13) 164.78, 164.30, 162.54, 132.57, 110.81, 104.64, 60.87, 59.83, 13.88, 13.84. MS (m/z) 244 [M+H]+.
1.828 g With sulfur; triethylamine In N,N-dimethyl-formamide at 60℃; for 5h; Diethyl 2-aminothiophene-3,4-dicarboxylate 0271] To a solution of ethyl pyruvate (1.778 mL, 16 mmol), ethyl cyanoacetate (2.388 mL, 22.4 mmol) and triethylamine (2.669 mL, 19.2 mmol) in N,N-dimethylformamide (8.0 mL) was added sulfur (564 mg, 17.6 mmol; finely ground using a mortar). The suspension was heated at 60° C. for 5 hours. The solvents were removed in vacuo and the slurry was dissolved in ethyl acetate. The organic solution was extracted successively with brine, saturated aqueous sodium bicarbonate solution, brine, hydrogen chloride (1N) and again brine. The organic fraction was dried over magnesium sulfate after which the solvent was removed in vacuo. The crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of heptane and ethyl acetate (in a ratio gradually ranging from 20% to 30% ethyl acetate in heptane), yielding the title compound (1.828 g) as a yellow powder. 13C NMR δ (75 MHz, CDCl3) 164.78, 164.30, 162.54, 132.57, 110.81, 104.64, 60.87, 59.83, 13.88, 13.84. MS (m/z) 244 [M+H]+.
  • 40
  • [ 104680-25-3 ]
  • C10H11ClO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 2-amine-thiophene-3,4-dicarboxylic acid ethyl ester With hydrogenchloride In water at 20℃; for 0.333333h; Stage #2: With sodium nitrite In water at 0℃; for 0.166667h; Stage #3: With copper(l) chloride In water for 0.75h;
  • 41
  • [ 104680-25-3 ]
  • C6HClO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water / 0.33 h / 20 °C 1.2: 0.17 h / 0 °C 1.3: 0.75 h 2.1: potassium hydroxide / water / 12 h / Reflux 2.2: 3 h / 140 °C
  • 42
  • [ 104680-25-3 ]
  • C7H3ClO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water / 0.33 h / 20 °C 1.2: 0.17 h / 0 °C 1.3: 0.75 h 2.1: potassium hydroxide / water / 12 h / Reflux 2.2: 3 h / 140 °C 3.1: ethyl acetate; triethylamine / 12 h / 65 °C
  • 43
  • [ 104680-25-3 ]
  • 2-(1-chloro-6-oxo-5,6-dihydro-4H-cyclopenta[c]thiophen-4-ylidene)malononitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water / 0.33 h / 20 °C 1.2: 0.17 h / 0 °C 1.3: 0.75 h 2.1: potassium hydroxide / water / 12 h / Reflux 2.2: 3 h / 140 °C 3.1: ethyl acetate; triethylamine / 12 h / 65 °C 4.1: sodium acetate / ethanol / 24 h / 20 °C
  • 44
  • [ 104680-25-3 ]
  • 4-oxo-3H,4H-thieno[2,3-d]pyrimidine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Sodium sulfate [anhydrous] 2: ammonia
Multi-step reaction with 2 steps 1: ethanol / 18 h / Reflux 2: calcium(II) chloride; ammonia / methanol; ethanol / 18 h / 60 °C
  • 45
  • [ 104680-25-3 ]
  • 3-({2-[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]-2H-1,2,3,4-tetrazol-5-yl}methyl)-4-oxo-3H,4H-thieno[2,3-d]pyrimidine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Sodium sulfate [anhydrous] 2: ammonia
Multi-step reaction with 3 steps 1: ethanol / 18 h / Reflux 2: calcium(II) chloride; ammonia / methanol; ethanol / 18 h / 60 °C 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C
  • 46
  • [ 3473-63-0 ]
  • [ 104680-25-3 ]
  • [ 1353498-44-8 ]
YieldReaction ConditionsOperation in experiment
With Sodium sulfate [anhydrous] Ethyl 4-oxo-3H,4H-thieno[2,3-d]pyrimidine-5-carboxylate Ethyl 4-oxo-3H,4H-thieno[2,3-d]pyrimidine-5-carboxylate A mixture of 13.9 g (57.14 mmol) diethyl 2-aminothiophene-3,4-dicarboxylate and 24.4 g (234.26 mmol) formamidinium acetate in 100 mL ethanol are refluxed under stirring for 18 h. After cooling to RT, the reaction mixture is concentrated under reduced pressure, treated with water, and extracted with EtOAc three times. Combined organic layers are treated with Na2SO4, filtered and concentrated under reduced pressure. The residue is treated with water and the precipitate is filtered off and dried to provide intermediate XII. C9H8N2O3S (M=224.24 g/mol) ESI-MS: 225 [M+H]+
In ethanol for 18h; Reflux; Ethyl 4-oxo-3H,4H-thieno[2,3-d]pyrimidine-5-carboxylate A mixture of 13.9 g (57.14 mmol) diethyl 2-aminothiophene-3,4-dicarboxylate and 24.4 g (234.26 mmol) formamidinium acetate in 100 mL ethanol are refluxed under stirring for 18 h. After cooling to RT, the reaction mixture is concentrated under reduced pressure, treated with water, and extracted with EtOAc three times. Combined organic layers are treated with Na2SO4, filtered and concentrated under reduced pressure. The residue is treated with water and the precipitate is filtered off and dried to provide intermediate XII. C9H8N2O3S (M=224.24 g/mol) ESI-MS: 225 [M+H]+ Rt (HPLC): 0.70 min (method H)
In ethanol for 18h; Reflux; Ethyl 4-oxo-3H,4H-thieno[2,3-d]pyrimidine-5-carboxylate A mixture of 13.9 g (57.14 mmol) diethyl 2-aminothiophene-3,4-dicarboxylate and 24.4 g (234.26 mmol) formamidinium acetate in 100 mL ethanol are refluxed under stirring for 18 h. After cooling to RT, the reaction mixture is concentrated under reduced pressure, treated with water, and extracted with EtOAc three times. Combined organic layers are treated with Na2SO4, filtered and concentrated under reduced pressure. The residue is treated with water and the precipitate is filtered off and dried to provide intermediate XII. C9H8N2O3S (M=224.24 g/mol) ESI-MS: 225 [M+H]+ Rt (HPLC): 0.70 min (method H)
  • 47
  • [ 104680-25-3 ]
  • None [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 18 h / Reflux 2: calcium(II) chloride; ammonia / methanol; ethanol / 18 h / 60 °C 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C
  • 48
  • [ 104680-25-3 ]
  • C19H14FN7O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 18 h / Reflux 2: calcium(II) chloride; ammonia / methanol; ethanol / 18 h / 60 °C 3: potassium carbonate / N,N-dimethyl acetamide / 20 °C
  • 49
  • [ 104680-25-3 ]
  • C19H14ClN7O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 18 h / Reflux 2: calcium(II) chloride; ammonia / methanol; ethanol / 18 h / 60 °C 3: potassium carbonate / N,N-dimethyl acetamide / 20 °C
  • 50
  • [ 104680-25-3 ]
  • C19H15N7O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 18 h / Reflux 2: calcium(II) chloride; ammonia / methanol; ethanol / 18 h / 60 °C 3: potassium carbonate / N,N-dimethyl-formamide / 50 °C
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