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[ CAS No. 1123-54-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1123-54-2
Chemical Structure| 1123-54-2
Structure of 1123-54-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1123-54-2 ]

CAS No. :1123-54-2 MDL No. :MFCD00005697
Formula : C4H4N6 Boiling Point : -
Linear Structure Formula :- InChI Key :HRYKDUPGBWLLHO-UHFFFAOYSA-N
M.W : 136.11 Pubchem ID :70746
Synonyms :

Calculated chemistry of [ 1123-54-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 33.88
TPSA : 93.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.17
Log Po/w (XLOGP3) : -0.96
Log Po/w (WLOGP) : -0.66
Log Po/w (MLOGP) : -0.83
Log Po/w (SILICOS-IT) : 0.14
Consensus Log Po/w : -0.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.75
Solubility : 24.5 mg/ml ; 0.18 mol/l
Class : Very soluble
Log S (Ali) : -0.52
Solubility : 41.5 mg/ml ; 0.305 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.4
Solubility : 5.37 mg/ml ; 0.0394 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 1123-54-2 ]

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

Application In Synthesis of [ 1123-54-2 ]

* 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 [ 1123-54-2 ]

[ 1123-54-2 ] Synthesis Path-Downstream   1~51

  • 2
  • [ 1123-54-2 ]
  • [ 23737-51-1 ]
  • [ 85446-49-7 ]
  • [ 85446-50-0 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate 1.) methanol, room temperature 2.) dimethylformamide, 8 h, 100 deg C; Yield given. Multistep reaction. Yields of byproduct given;
  • 3
  • [ 4330-21-6 ]
  • [ 1123-54-2 ]
  • 7-amino-2-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-2H-1,2,3-triazolo<4,5-d>pyrimidine [ No CAS ]
  • [ 127302-87-8 ]
  • [ 127277-97-8 ]
  • [ 127278-00-6 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 13% 3: 12% 4: 11% With potassium carbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; Further byproducts given;
  • 4
  • [ 4330-21-6 ]
  • [ 1123-54-2 ]
  • [ 127302-87-8 ]
  • 7-amino-4-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4H-1,2,3-triazolo<4,5-d>pyrimidine [ No CAS ]
  • [ 127277-97-8 ]
  • [ 127278-00-6 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 13% 3: 12% 4: 3% With potassium carbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; Further byproducts given;
  • 5
  • [ 4330-21-6 ]
  • [ 1123-54-2 ]
  • [ 127302-87-8 ]
  • 7-amino-4-<2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-4H-1,2,3-triazolo<4,5-d>pyrimidine [ No CAS ]
  • [ 127277-97-8 ]
  • [ 127278-00-6 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 13% 3: 12% 4: 4% With potassium carbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; Further byproducts given;
  • 6
  • [ 5122-82-7 ]
  • [ 1123-54-2 ]
  • [ 124558-97-0 ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; for 7h;
  • 7
  • [ 53-84-9 ]
  • [ 1123-54-2 ]
  • adenosine 5′-diphosphate ribose [ No CAS ]
  • 8-aza-9H-adenine adenine dinucleotide ammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With sodium hydroxide; NAD nucleosidase; tris hydrochloride In water at 37℃; for 30h; pH: 7.2;
  • 8
  • [ 131487-19-9 ]
  • [ 1123-54-2 ]
  • [ 145307-47-7 ]
  • [ 145259-67-2 ]
  • 7-Amino-2-<2,3-dideoxy-5-O-<(1,1-dimethylethyl)dimethylsilyl>-D-glycero-pentofuranosyl>-2H-1,2,3-triazolo<4,5-d>pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 9.3% 2: 13.9% 3: 8.5% With Tris(3,6-dioxaheptyl)amine; potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Ambient temperature;
  • 9
  • [ 116384-58-8 ]
  • [ 1123-54-2 ]
  • 7-amino-3-<2-(diethylphosphonomethoxy)ethyl>-3H-1,2,3-triazolo<4,5-d>pyrimidine [ No CAS ]
  • [ 158780-68-8 ]
  • 7-amino-1-<2-(diethylphosphonomethoxy)ethyl>-1H-1,2,3-triazolo<4,5-d>pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 5% 3: 34% With sodium hydride In N,N-dimethyl-formamide; paraffin at 80℃; for 14h;
  • 10
  • [ 116384-58-8 ]
  • [ 1123-54-2 ]
  • 7-amino-1-<2-(diethylphosphonomethoxy)ethyl>-1H-1,2,3-triazolo<4,5-d>pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% With sodium hydride In N,N-dimethyl-formamide; paraffin at 80℃; for 14h;
  • 11
  • [ 1123-54-2 ]
  • [ 77-78-1 ]
  • [ 77022-74-3 ]
  • [ 6312-55-6 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In water at 40℃; for 1h; Title compound not separated from byproducts;
  • 12
  • [ 1123-54-2 ]
  • [ 74-88-4 ]
  • 3,7-dimethyl-8-azaadeninium iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% In N,N-dimethyl-formamide at 100℃; for 1h; closed vessel;
  • 13
  • [ 951-78-0 ]
  • [ 1123-54-2 ]
  • 8-Aza-2'-deoxy-adenosine [ No CAS ]
  • 2'-deoxy-8-azainosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 37℃; for 16h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.7;
  • 14
  • [ 1123-54-2 ]
  • [ 4909-78-8 ]
  • 8-aza-N6-dimethylaminomethyleneadenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In N,N-dimethyl-formamide at 100℃; for 16h;
  • 15
  • [ 127682-77-3 ]
  • [ 1123-54-2 ]
  • [ 163667-60-5 ]
  • [ 163667-57-0 ]
YieldReaction ConditionsOperation in experiment
With 18-crown-6 ether; potassium carbonate 1.) DMF, RT, 30 min, 2.) DMF, 75 deg C, 17 h; Yield given. Multistep reaction. Yields of byproduct given;
  • 16
  • [ 143191-76-8 ]
  • [ 1123-54-2 ]
  • Benzoic acid (2S,4S)-4-(7-amino-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • Benzoic acid (2S,4S)-4-(7-amino-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 70℃; for 20h;
  • 17
  • [ 1123-54-2 ]
  • [ 151965-56-9 ]
  • 9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-8-azaadenine [ No CAS ]
  • [2-(7-Amino-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 26% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;
  • 18
  • [ 1123-54-2 ]
  • [ 146459-58-7 ]
  • [(S)-2-(7-Amino-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-1-fluoromethyl-ethoxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
  • [(S)-2-(7-Amino-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-1-fluoromethyl-ethoxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 35% 2: 22% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;
  • 19
  • [ 1123-54-2 ]
  • [ 141110-74-9 ]
  • [(S)-2-(7-Amino-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
  • [(S)-2-(7-Amino-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 0.76 g 2: 0.8 g With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;
  • 20
  • [ 1123-54-2 ]
  • [ 160616-47-7 ]
  • [(R)-2-(7-Amino-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
  • [(R)-2-(7-Amino-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 22% 2: 37% With caesium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 6h;
  • 21
  • [ 1123-54-2 ]
  • [ 23788-74-1 ]
  • 3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
  • 1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
  • 2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 22% 2: 4% 3: 20% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 20h;
  • 22
  • [ 1123-54-2 ]
  • [ 870-63-3 ]
  • 2-(3-Methyl-but-2-enyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
  • 1-(3-Methyl-but-2-enyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
  • 3-(3-Methyl-but-2-enyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1.) DMF, RT, 20 min, 2.) DMF, RT, 5 h; Yield given. Multistep reaction. Yields of byproduct given;
  • 23
  • [ 19206-69-0 ]
  • [ 1123-54-2 ]
  • 2-Allyl-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
  • 3-Allyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium hydride 1.) DMF, 60 deg C oil bath, 2.) DMF, 60 deg C; Yield given. Multistep reaction. Yields of byproduct given;
  • 24
  • [ 58329-99-0 ]
  • [ 1123-54-2 ]
  • 2-Cyclohex-2-enyl-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
  • 3-Cyclohex-2-enyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium hydride 1.) DMF, 60 deg C oil bath, 2.) DMF, 60 deg C; Yield given. Multistep reaction. Yields of byproduct given;
  • 25
  • [ 1123-54-2 ]
  • cis-<4-<(methoxycarbonyl)oxy>-2-cyclohexen-1-yl>methylcarbonic acid methyl ester [ No CAS ]
  • Carbonic acid 4-(7-amino-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-cyclohex-2-enylmethyl ester methyl ester [ No CAS ]
  • Carbonic acid 4-(7-amino-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-cyclohex-2-enylmethyl ester methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium hydride 1.) DMF, 60 deg C oil bath, 2.) DMF, 60 deg C; Yield given. Multistep reaction. Yields of byproduct given;
  • 26
  • [ 1123-54-2 ]
  • Carbonic acid (1S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-2-enyl ester methyl ester [ No CAS ]
  • 3-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclohex-2-enyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
  • 2-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclohex-2-enyl]-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium hydride 1.) DMF, 60 deg C oil bath, 2.) DMF, 60 deg C; Yield given. Multistep reaction. Yields of byproduct given;
  • 27
  • [ 1123-54-2 ]
  • [ 13035-61-5 ]
  • [ 92516-90-0 ]
  • 7-Amino-2-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]-2H-1,2,3-triazolo[4,5-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 34% With tin(IV) chloride In acetonitrile for 24h; Ambient temperature;
With tin(IV) chloride In acetonitrile at 95℃; for 6h; various temperatures investigated;
  • 28
  • [ 1123-54-2 ]
  • t-butyl (+/-)-(1S,4R)-2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate [ No CAS ]
  • (+/-)-(1'β,4'β)-Δ2',3'-4'-(hydroxy-tert-butoxycarbonylamino)-1'-(8-azaadenin-8-yl)-cyclopentene [ No CAS ]
  • (+/-)-(1'β,4'β)-Δ2',3'-4'-(hydroxy-tert-butoxycarbonylamino)-1'-(8-azaadenin-9-yl)-cyclopentene [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 39% 2: 24% With tetrakis(triphenylphosphine) palladium(0); lithium hydride In dimethyl sulfoxide at 22℃; for 4h;
  • 29
  • [ 1123-54-2 ]
  • [ 292864-77-8 ]
  • [ 292864-80-3 ]
  • [ 292864-81-4 ]
YieldReaction ConditionsOperation in experiment
1: 50% 2: 23% With triphenylphosphine; diethylazodicarboxylate In 1,4-dioxane at 20℃; for 22h;
  • 30
  • [ 1123-54-2 ]
  • C4H5N6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With dinitrogen monoxide In water Radiolysis;
  • 31
  • [ 1123-54-2 ]
  • [ 999-97-3 ]
  • C13H28N6Si3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium sulfate at 140℃; for 1.5h; 1; 4 Example 1; Scheme 2; Benzoic acid 2-(7-amino-[l,2,3]triazolo[4,5-d]pyiliiiidin-3-yI)-5-(diethoxy- phosphoiylmethoxy)-tetrahydrofyian-3-yl ester, (2.1) and benzoic acid 2-(7- ainino-[l,2,3]triazolo[4,5-d]pyrintidin-2-yl)-5-(diethoxy-phosphorylinethoxy)- tetrahydrofyran-3-yl ester (2.2); 10 A 1,1,1,3,3,3-hexarnethyldisilazane suspension (10 mL) of 8-azaadenine (0.25 g, 1.8 mmol) and ammonium sulfate (0.16 g, 1.2 mmol) was heated at 1400C for 1.5 h. The resulting clear solution was concentrated to dryness and azeotroped with acetonitrile twice. The solution of the persilylated 8-azaadenine was added to phosphonate 1.7 (see scheme 1) (0.5 g, 1.2 mmol) in acetonitrile (10 mL), and the15 resultant solution then treated with BF3.Et2θ (0.24 mL, 1.8 mmol). The resulting solution was heated at 45 °C for 1.5 h and then concentrated to dryness. The crude residue was purified by C-18 HPLC to afford the title compound 2.1 (0.16 g/37 %) and 2.2 (0.07 g, 12 %). Compound 2.1 1H NMR (CDCIs): δ 8.45 (s, IH), 8.00 (d, 2H, J= 8.0), 7.56 (t, IH, J = 7.3), 7.42 (t, 2H, J = 7.6), 6.68 (d, IH, J= 1.9),20 6.49-6.54 (m, IH), 5.60-5.70 (m, IH), 4.01-4.18 (m, 4H), 3.64-3.80 (m, 2H), 3.08-3.17 (m, IH), 2.64-2.72 (m, IH), 1.20-1.34 (2t,6H). 31P NMR: 20.55 ppm. Compound 2.2 1H NMR (CDCl3): δ 8.48(s, IH), 8.00 (d, 2H, J = 8.0), 7.59 (t, IH, J = 7.6), 7.42 (t, 2H, J = 7.6), 6.65 (d, IH, J= 3.3), 6.15-6.21 (m, IH), 5.55 (m, lH), 4.04-4.22 (m, 5H), 3.69 (t, IH, J = 2.4),.2.94-3.01 (m, IH), 2.49-2.60 (m, IH), 1.20-1.34 (2t, 6H).31P NMR:25 20.68 ppm.; Acetate 6.6 is then reacted with a silylated nucleobase, for example silylated 8-azaadenine prepared from the treatment of 8-aza adenine with hexamethyldisilazide and ammonium sulfate, in the20 presence of a Lewis acid e.g. BFsOEt to afford the nucleoside phosphonate 6.7.
  • 32
  • [ 1123-54-2 ]
  • [ 2074-87-5 ]
YieldReaction ConditionsOperation in experiment
In gaseous matrix film formation by 350-1000 eV Ar(1+)-beam sputtering from organic compd.target onto substrate (Si, Cu, Ag, Co, Ni, stainless steel) below 100.d egree.C for 30 and 120 min;
  • 33
  • [ 1184-57-2 ]
  • [ 1123-54-2 ]
  • d}{(CH3Hg) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water addn. of CH3HgOH to aadH suspn. in a well ventilated fume hood; heating, 50-60°C, 1-3h; adjusting pH to 6-7 by HNO3; cooling or slow evapn.; filtration; washing with ethanol or ether; elem. anal.;
  • 34
  • [ 1184-57-2 ]
  • [ 1123-54-2 ]
  • dH(-1)}{(CH3Hg)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water addn. of CH3HgOH to aadH suspn. in a well ventilated fume hood; heating, 50-60°C, 1-3h; adjusting pH >=7 by NaOH; cooling or slow evapn.; filtration; washing with ethanol or ether; elem. anal.;
  • 35
  • [ 1184-57-2 ]
  • [ 1123-54-2 ]
  • dH}NO3{(CH3Hg) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water addn. of CH3HgOH to aadH suspn. in a well ventilated fume hood; heating, 50-60°C, 1-3h; adjusting pH <2 by HNO3; cooling or slow evapn.; filtration; washing with ethanol or ether; elem. anal.;
With HNO3 In water; nitric acid aq. HNO3; HgCH3(OH) added to a suspension of 8-azaadenine (1:1, pH=2); evapn. (slowly, room temp.), crystn. (over a period of several weeks);
  • 36
  • [ 1184-57-2 ]
  • [ 1123-54-2 ]
  • dH(-1)}NO3{(CH3Hg)3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water addn. of CH3HgOH to aadH suspn. in a well ventilated fume hood; heating, 50-60°C, 1-3h; adjusting pH to 4.5-6.5 by HNO3; cooling or slow evapn.; filtration; washing with ethanol or ether; elem. anal.;
With H2O; HNO3 In nitric acid aq. HNO3; HgCH3(OH) added to a suspension of 8-azaadenine (3:1, pH=6.5); evapn. (slowly, room temp.), crystn. (over a period of several weeks);
  • 37
  • [ 1184-57-2 ]
  • [ 1123-54-2 ]
  • d}NO3*H2O{(CH3Hg)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water addn. of CH3HgOH to aadH suspn. in a well ventilated fume hood; heating, 50-60°C, 1-3h; adjusting pH to 1-5 by HNO3; cooling or slow evapn.; filtration; washing with ethanol or ether; elem. anal.;
With H2O; HNO3 In nitric acid aq. HNO3; HgCH3(OH) added to a suspension of 8-azaadenine (2:1, pH=5); evapn. (slowly, room temp.), crystn. (over a period of several weeks);
  • 38
  • copper(II) nitrate [ No CAS ]
  • [ 1123-54-2 ]
  • {Cu(H2O)4(8-aza-adenine)2}(NO3)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In nitric acid aq. HNO3; addn. of 1M HNO3 with stirring to a suspension of 8-azaadenine in H2O containing Cu(NO3)2 until soln. was achieved; pH was adjusted to 2 with NaOH;; crystn. on standing over a period of 3-5 days; elem. anal.;
  • 39
  • [ 1123-54-2 ]
  • [ 7646-85-7 ]
  • Zn(2+)*2C4H4N6*2Cl(1-)*H2O=Zn(C4H4N6)2Cl2*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hydrogenchloride gradually adding and stirring an acidic soln. of ZnCl2 into a soln. of 8-azaadenine; standing under refrigeration, pptn., filtn., washing with water and alcohol, drying in vacuum over P2O5, elem. anal.;
  • 40
  • [ 10025-99-7 ]
  • [ 1123-54-2 ]
  • Pt(2+)*2C4H4N6*2Cl(1-)=Pt(C4H4N6)2Cl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water gradually adding and stirring a soln. of K2PtCl4 into a suspn. of 8-azaadenine in water, stirring for 3 days, colour changes to yellow, pptn.; filtn., washing with water and alcohol, drying in vacuum over P2O5, elem. anal.;
  • 41
  • [ 1184-57-2 ]
  • [ 1123-54-2 ]
  • C4HN5(NH2)(HgCH3)*4H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With H2O In nitric acid aq. HNO3; HgCH3(OH) added to a suspension of 8-azaadenine (1:1, pH=5); evapn. (slowly, room temp.), crystn. (over a period of several weeks);
  • 42
  • [ 1123-54-2 ]
  • mercury dichloride [ No CAS ]
  • [ 77495-61-5 ]
YieldReaction ConditionsOperation in experiment
In hydrogenchloride; water aq. soln. of HgCl2 was added to soln. of ligand in aq. HCl, mixt. was heated to 35°C, allowed to cool slowly; filtered, air dried; elem. anal.;
  • 43
  • [ 901776-30-5 ]
  • [ 1123-54-2 ]
  • (2S,3S,4R)-2-((3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-methoxy-4-oxobutylthio)methyl)-5-(7-amino-2H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)tetrahydrofuran-3,4-diyl diacetate [ No CAS ]
  • C33H35N7O9S [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 33 mg With tin(IV) chloride In dichloromethane; acetonitrile at 20℃; for 24h; Inert atmosphere;
  • 44
  • D-2-deoxyribose [ No CAS ]
  • [ 1123-54-2 ]
  • 8-Aza-2'-deoxy-adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% With purine nucleoside phosphorylase; phosphopentomutase; ribokinase; potassium chloride; ATP; manganese(ll) chloride at 40℃; for 15h; aq. buffer; Enzymatic reaction; regiospecific reaction;
  • 45
  • [ 961-07-9 ]
  • [ 1123-54-2 ]
  • 8-Aza-2'-deoxy-adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With purine nucleoside phosphorylase at 50℃; aq. phosphate buffer; Enzymatic reaction;
  • 46
  • [ 1123-54-2 ]
  • [ 951-77-9 ]
  • 8-Aza-2'-deoxy-adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With purine nucleoside phosphorylase In dimethyl sulfoxide at 50℃; for 72h; aq. phosphate buffer; Enzymatic reaction;
  • 47
  • [ 32315-10-9 ]
  • (4S)-7-chloro-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b] [1,4]diazepine [ No CAS ]
  • [ 1123-54-2 ]
  • (4S)-N-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-7-chloro-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20.63% Stage #1: bis(trichloromethyl) carbonate; (4S)-7-chloro-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b] [1,4]diazepine In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 7-amino-1H-triazolo[4,5-d]pyrimidine With triethylamine In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Synthesis of (4S)-N-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-7-chloro-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide To a solution of (4S)-7-chloro-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine (500 mg, 2.56 mmol) in Tetrahydrofuran (THF) (10 mL) stirred under nitrogen at room temp was added triphosgene (758 mg, 2.56 mmol) and stirred for 30 min at RT, then triethylamine (0.356 mL, 2.56 mmol) and 3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine (417 mg, 3.07 mmol) were added. The reaction mixture was stirred at 60° C. for 16 hr. The reaction was monitored by TLC (10% Methanol in DCM). The reaction mixture was quenched with 25 ml of water and extracted with 25 ml of ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford the crude compound. The crude product was added to a 100-200 silica gel column and was eluted with 3% DCM/MeOH to afford pure compound (4S)-N-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-7-chloro-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (200 mg, 0.527 mmol, 20.63% yield) as an off white solid, LCMS (m/z) 357.9 [M+H]+.
20.63% Stage #1: bis(trichloromethyl) carbonate; (4S)-7-chloro-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b] [1,4]diazepine In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 7-amino-1H-triazolo[4,5-d]pyrimidine With triethylamine In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Synthesis of (4S)-N-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-7-chloro-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide To a solution of (4S)-7-chloro-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3-b][l,4]diazepine (500 mg, 2.56 mmol) in Tetrahydrofuran (THF) (10 mL) stirred under nitrogen at room temp was added triphosgene (758 mg, 2.56 mmol) and stirred for 30 min at RT, then triethylamine (0.356 mL, 2.56 mmol) and 3H-[l,2,3]triazolo[4,5-d]pyrimidin-7-amine (417 mg, 3.07 mmol) were added. The reaction mixture was stirred at 60 °C for 16 hr. The reaction was monitored by TLC(10% Methanol in DCM). The reaction mixture was quenched with 25 ml of water and extracted with 25 ml of ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford the crude compound. The crude product was added to a 100-200 silica gel column and was eluted with 3% DCM/MeOH to afford pure compound (4S)-N-(3H-[l,2,3]triazolo[4,5- d]pyrimidin-7-yl)-7-chloro-3,4-dihydro-l,4-methanopyrido[2,3-b][l,4]diazepine-5(2H)- carboxamide (200 mg, 0.527 mmol, 20.63 % yield) as an off white solid, LCMS (m/z) 357.9 [M+H]+.
  • 48
  • [ 1123-54-2 ]
  • [ 151965-56-9 ]
  • 9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-8-azaadenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃;
  • 49
  • [ 55368-24-6 ]
  • [ 1123-54-2 ]
  • C14H14N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In N,N-dimethyl-formamide at 80℃;
  • 50
  • cis-3-methylcyclohexan-1-ol [ No CAS ]
  • [ 1123-54-2 ]
  • (±)-3-(trans-3-methylcyclohexyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With (trimethyl-λ5-phosphanyliden)acetonitrile In 1,4-dioxane at 110℃; for 4h; Inert atmosphere; 94 Preparation of 3-[trans-3-methylcyclohexyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine Example 94 Preparation of 3-[trans-3-methylcyclohexyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine trans, racemate A mixture of 3H-triazolo[4,5-d]pyrimidin-7-amine (140 mg), cis-3-methylcyclohexanol (352 mg), and 1,4-dioxane (50 mL) was subjected to nitrogen replacement, then to the mixture was added cyanomethylenetrimethylphosphorane (355 mg), and the resulting mixture was stirred at 110° C. for 4 hours. The reaction mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (solvent: hexane/ethyl acetate=40/60 to 0/100) to give the title compound (122 mg) (yield 51%) as a colorless powder. MS(APCI) m/z: 233 [M+H]+
  • 51
  • [ 97614-44-3 ]
  • [ 1123-54-2 ]
  • (2R,3R,4S,5R)-5-(7-amino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2-((benzoyloxy)methyl)-4-fluorotetrahydrofuran-3-yl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-amino-1H-triazolo[4,5-d]pyrimidine With sodium hydride In 1-methyl-pyrrolidin-2-one for 1h; Stage #2: 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide In 1-methyl-pyrrolidin-2-one for 18h; 13.1 Step 1: (2R,3R,4S,5R)-5-(7-amino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2- ((benzoyloxy)methyl)-4-fluorotetrahydrofuran-3-yl benzoate To a mixture of 3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine (2.36g, 17.4mmol) in NMP (50mL) was added NaH (60%, 0.744g, 18.6 mmol). The mixture was vigorously stirred, and after 1h, generation of bubbles had completely ceased. The mixture was added to ((2R,3R,4S,5R)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (neat, 5.25g, 12.4mmol) in one portion. It was stirred for 18h. LCMS showed several peaks with the desired mass (m/e=479). EtOAc (70mL) and H2O (70mL) were added to the reaction. Layers were separated, and the organic layer was washed with half saturated brine (3x10mL) and brine (1x10mL), dried (MgSO4), and concentrated. The crude was purified via silica column eluting with 0 to 50% EtOAc in Hex to give the product. LCMS (ES, m/z): 479.3 [M+H]+.1H-NMR (500MHz, DMSO-d6): δ 8.62 (s, 1H), 8.34 (s, 1H), 8.28 (s, 1H), 8.10-8.04 (m, 2H), 7.97-7.90 (m, 2H), 7.77-7.69 (m, 1H), 7.67-7.55 (m, 3H), 7.49-7.42 (m, 2H), 6.97 (dd, J=6.5, 3.1Hz, 1H), 6.49 (dt, J=17.6, 6.9Hz, 1H), 6.16 (dt, J=56, 6.6Hz, 1H), 4.76-4.62 (m, 3H).
Stage #1: 7-amino-1H-triazolo[4,5-d]pyrimidine With sodium hydride In 1-methyl-pyrrolidin-2-one; mineral oil for 1h; Stage #2: 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide In 1-methyl-pyrrolidin-2-one; mineral oil for 18h; 2.1 Step 1: (2R,3R,4S,5R)-5-(7-amino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2- ((benzoyloxy)methyl)-4-fluorotetrahydrofuran-3-yl benzoate To a mixture of 3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine (2.36g, 17.4mmol) in N- methyl-2-pyrrolidone (50mL) was added NaH (60%, 0.744g, 18.6mmol). The mixture was vigorously stirred and after 1h, generation of bubbles had completely ceased. The mixture was added to ((2R,3R,4S,5R)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (neat, 5.25g, 12.4mmol) in one portion. It was stirred for 18h. Then, EtOAc (70mL) and water (70mL) were added to the reaction. The layers were separated, and the organic layer was washed with half-saturated brine (3×10mL) and brine (1×10mL), dried (MgSO4), and concentrated. The crude was purified by silica column chromatography eluted with 0 to 50% EtOAc in Hex to give the product. LCMS (ES, m/z): 479.3 [M+H]+.1H-NMR (500MHz, DMSO-d6): d 8.62 (s, 1H), 8.34 (s, 1H), 8.28 (s, 1H), 8.10-8.04 (m, 2H), 7.97-7.90 (m, 2H), 7.77-7.69 (m, 1H), 7.67-7.55 (m, 3H), 7.49-7.42 (m, 2H), 6.97 (dd, J=6.5, 3.1Hz, 1H), 6.49 (dt, J=17.6, 6.9Hz, 1H), 6.16 (dt, J=56, 6.6Hz, 1H), 4.76-4.62 (m, 3H).
Stage #1: 7-amino-1H-triazolo[4,5-d]pyrimidine With sodium hydride In 1-methyl-pyrrolidin-2-one for 1h; Stage #2: 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide In 1-methyl-pyrrolidin-2-one for 18h; 2.1 Step 1: (2R,3R,4S,5R)-5-(7-amino-3H-1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2-((benzoyloxy)methyl)-4-fluorotetrahydrofuran-3-yl benzoate To a mixture of 3H-[l,2,3]triazolo[4,5-d]pyrimidin-7-amine (2.36g, 17.4mmol) in N- methyl-2-pyrrolidone (50mL) was added NaH (60%, 0.744g, 18.6mmol). The mixture was vigorously stirred and after lh, generation of bubbles had completely ceased. The mixture was added to ((2R,3R,4S,5R)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (neat, 5.25g, 12.4mmol) in one portion. It was stirred for 18h. Then, EtOAc (70mL) and water (70mL) were added to the reaction. The layers were separated, and the organic layer was washed with half-saturated brine (3xl0mL) and brine (l x lOmL), dried (MgS04), and concentrated. The crude was purified by silica column chromatography eluted with 0 to 50% EtOAc in Hex to give the product. LCMS (ES, m/z): 479.3 [M+H]+. -NMR (500MHz, DMSO-de): d 8.62 (s, 1H), 8.34 (s, 1H), 8.28 (s, 1H), 8.10-8.04 (m, 2H), 7.97-7.90 (m, 2H), 7.77-7.69 (m, 1H), 7.67-7.55 (m, 3H), 7.49-7.42 (m, 2H), 6.97 (dd, J=6.5, 3.1Hz, 1H), 6.49 (dt, J=17.6, 6.9Hz, 1H), 6.16 (dt, J=56, 6.6Hz, 1H), 4.76-4.62 (m, 3H).
Stage #1: 7-amino-1H-triazolo[4,5-d]pyrimidine With sodium hydride In 1-methyl-pyrrolidin-2-one; mineral oil for 1h; Stage #2: 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide In 1-methyl-pyrrolidin-2-one; mineral oil for 18h; 2.1 Step 1: (2R,3R,4S,5R)-5-(7-amino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2-((benzoyloxy)methyl)-4-fluorotetrahydrofuran-3-yl benzoate To a mixture of 3H-[l,2,3]triazolo[4,5-d]pyrimidin-7-amine (2.36g, 17.4mmol) in N- methyl-2-pyrrolidone (50mL) was added NaH (60%, 0.744g, 18.6mmol). The mixture was vigorously stirred, and after lh, generation of bubbles had completely ceased. The mixture was added to ((2R,3R,4S,5R)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (neat, 5.25g, 12.4mmol) in one portion. It was stirred for 18h. Then, EtOAc (70mL) and water (70mL) were added to the reaction. The layers were separated, and the organic layer was washed with half-saturated brine (3xl0mL) and brine (l x lOmL), dried (MgSOr). and concentrated. The crude was purified by silica column chromatography eluted with 0 to 50% EtOAc in Hex to give the product. LCMS (ES, m/z): 479.3 [M+H]+. -NMR (500MHz, DMSO-de): d 8.62 (s, 1H), 8.34 (s, 1H), 8.28 (s, 1H), 8.10-8.04 (m, 2H), 7.97-7.90 (m, 2H), 7.77-7.69 (m, 1H), 7.67-7.55 (m, 3H), 7.49-7.42 (m, 2H), 6.97 (dd, J=6.5, 3.1Hz, 1H), 6.49 (dt, J=17.6, 6.9Hz, 1H), 6.16 (dt, J=56, 6.6Hz, 1H), 4.76-4.62 (m, 3H).

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