Home Cart 0 Sign in  
X

[ CAS No. 156-81-0 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 156-81-0
Chemical Structure| 156-81-0
Structure of 156-81-0 * Storage: {[proInfo.prStorage]}

Quality Control of [ 156-81-0 ]

Related Doc. of [ 156-81-0 ]

SDS
Alternatived Products of [ 156-81-0 ]
Alternatived Products of [ 156-81-0 ]

Product Details of [ 156-81-0 ]

CAS No. :156-81-0 MDL No. :MFCD00038023
Formula : C4H6N4 Boiling Point : 401.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :110.12 g/mol Pubchem ID :67431
Synonyms :

Safety of [ 156-81-0 ]

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 [ 156-81-0 ]

  • Upstream synthesis route of [ 156-81-0 ]
  • Downstream synthetic route of [ 156-81-0 ]

[ 156-81-0 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 1004-01-9 ]
  • [ 73183-34-3 ]
  • [ 156-81-0 ]
  • [ 944401-61-0 ]
YieldReaction ConditionsOperation in experiment
27% With potassium acetate In 1,4-dioxane at 115℃; for 16 h; Method 12; Synthesis of 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine-2,4-diamine; [0252] To a dry 1 L flask was added 5-bromopyrimidine-2,4-diamine (30.0 g, 158.7 mmol), potassium acetate (45.8 g, 466.7 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (51.16g g, 202.2 mmol) and dioxane (50O mL). Argon was bubbled through the solution for 15 minutes, at which time l,l'-bis(diphenylphosphino)ferrocene palladium(II) chloride (2.53 g, 3.11 mmol) was added. The reaction was refluxed in a 115 0C oil bath for 16 hours under argon. After cooling to room temperature, the solid inorganic material was filtered, rinsed with EtOAc (1 L). The organic filtrate was concentrated in vacuo and to the resulting solid was added dichloromethane (1 L). After sonication the solid was filtered. The solid was the debrominated 2,4-diaminopyrimidine. The filtrate containing desired boronate ester was concentrated in vacuo. To this residue was added diethyl ether (10O mL). After <n="66"/>sonication, the solution was filtered, rinsed with additional diethyl ether (50 mL) and the solid obtained was dried under high vacuum to yield the desired 2,4-diaminopyrimidyl-5- boronate ester (10.13 g, 27percent). By 1H NMR the material was a 4:1 mixture of 2,4- diaminopyrimidyl-5-boronate ester and 2,4-diaminopyrimidine byproduct. The material was used as is in subsequent Suzuki reactions LCMS (m/z): 155 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC); 1H NMR (CDCI3+CD3OD): δ 8.16 (s, IH), 1.34 (s, 12H).
Reference: [1] Patent: WO2008/98058, 2008, A1, . Location in patent: Page/Page column 64-65
[2] Patent: WO2007/84786, 2007, A1, . Location in patent: Page/Page column 98
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
[4] Patent: WO2012/109423, 2012, A1, . Location in patent: Page/Page column 23
  • 2
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 113-00-8 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 57-13-6 ]
YieldReaction ConditionsOperation in experiment
0.1 mg With manganese(II) chloride tetrahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 3
  • [ 156667-51-5 ]
  • [ 58243-08-6 ]
  • [ 50-01-1 ]
  • [ 156-81-0 ]
Reference: [1] Patent: US5521192, 1996, A,
  • 4
  • [ 3993-78-0 ]
  • [ 156-81-0 ]
Reference: [1] Patent: US2416617, 1944, ,
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 3758,3760
  • 5
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18514-52-8 ]
YieldReaction ConditionsOperation in experiment
0.18 mg With ferric sulfate nonahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 6
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
YieldReaction ConditionsOperation in experiment
0.12 mg With magnesium sulfate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 7
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 120-89-8 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
YieldReaction ConditionsOperation in experiment
1.6 mg With copper(II) choride dihydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 8
  • [ 2032-34-0 ]
  • [ 50-01-1 ]
  • [ 156-81-0 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 2587,2593
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 1, p. 240 - 253
  • 9
  • [ 3934-20-1 ]
  • [ 156-81-0 ]
Reference: [1] Journal of the Chemical Society, 1948, p. 2240,2246
[2] Journal of the Society of Chemical Industry, London, 1950, vol. 69, p. 353
  • 10
  • [ 156-83-2 ]
  • [ 156-81-0 ]
Reference: [1] Chemische Berichte, 1903, vol. 36, p. 2234
[2] Chemische Berichte, 1903, vol. 36, p. 2234
  • 11
  • [ 98198-74-4 ]
  • [ 156-81-0 ]
Reference: [1] American Chemical Journal, 1905, vol. 34, p. 190
  • 12
  • [ 13233-20-0 ]
  • [ 156-81-0 ]
  • [ 50574-59-9 ]
  • [ 65-46-3 ]
Reference: [1] Nature Chemistry, 2017, vol. 9, # 4, p. 303 - 309
  • 13
  • [ 727651-44-7 ]
  • [ 156-81-0 ]
Reference: [1] Chemische Berichte, 1903, vol. 36, p. 2234
  • 14
  • [ 67-56-1 ]
  • [ 155-90-8 ]
  • [ 7664-41-7 ]
  • [ 156-81-0 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 99
  • 15
  • [ 98198-74-4 ]
  • [ 156-81-0 ]
Reference: [1] American Chemical Journal, 1905, vol. 34, p. 190
  • 16
  • [ 3934-20-1 ]
  • [ 7664-41-7 ]
  • [ 7758-99-8 ]
  • [ 108-95-2 ]
  • [ 156-81-0 ]
Reference: [1] Journal of the Society of Chemical Industry, London, 1950, vol. 69, p. 353
  • 17
  • [ 7647-01-0 ]
  • [ 156-83-2 ]
  • [ 156-81-0 ]
Reference: [1] Chemische Berichte, 1903, vol. 36, p. 2234
  • 18
  • [ 156-81-0 ]
  • [ 68-12-2 ]
  • [ 20781-06-0 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: at 25℃; for 0.25 h; Cooling with ice
Stage #2: at 0 - 25℃; for 24 h;
General procedure: Vilsmeier reagent was prepared by mixing ice-cold dry DMF (50 ml) and POCl3 (30.0 mmol, 2.8 ml). The mixture was stirred for 15 min at 25 °C. To the previous mixture, aminopyrimidines (10.0 mmol) in dry DMF (5.0 ml) were added over a period of 15 min at 0-5 °C. The reaction mixturewas stirred for 24 h at 25 °C.The mixture was then added to cold, saturated aq. K2CO3 andextracted with diethyl ether. The organic layer was washed withwater, dried over anhydrous Na2SO4, and evaporated underreduced pressure to afford the crude product, whichwas purified ina silica gel column chromatography using hexane/ethyl acetate(9:1) as an eluent to give the title compounds 2 and 8. 4.3.1. 2,4-Diaminopyrimidine-5-carbaldehyde (2) Brown powder, yield 59percent; 1H-NMR [DMSO-d6, 400 MHz]: (δ,ppm) 7.10 (d, 2H, NH2, exchange with D2O), 7.52 (d, 2H, NH2, exchangewith D2O), 8.32 (s, 1H, H6-pyrimidine), 9.45 (CHO); 13C NMR[DMSO-d6, 100 MHz]: (δ, ppm) 106.2 (C5-pyrimidine), 162.7(C4-pyrimidine), 164.4 (C6-pyrimidine), 167.0 (C2-pyrimidine),189.5 (CHO).
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 270 - 282
  • 19
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 113-00-8 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 57-13-6 ]
YieldReaction ConditionsOperation in experiment
0.1 mg With manganese(II) chloride tetrahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 20
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 120-89-8 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
YieldReaction ConditionsOperation in experiment
1.6 mg With copper(II) choride dihydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 21
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18514-52-8 ]
YieldReaction ConditionsOperation in experiment
0.18 mg With ferric sulfate nonahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 22
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
YieldReaction ConditionsOperation in experiment
0.12 mg With magnesium sulfate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 23
  • [ 156-81-0 ]
  • [ 157924-46-4 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With Iodine monochloride In methanol at 25℃; for 15 h;
Stage #2: With sodium hydroxide In water at 25℃; for 2 h;
To a flame-dried 100 mL round-bottom flask was added 2,4-diaminopyrimidine (1.0 g, 9.08 mmol) in MeOH (30 mL) followed by dropwise addition of ICl (30 mL, 29.06 mmol). The solution was stirred at 25° C. for 15 h and then the solvent removed under reduced pressure. The resulting viscous oil was stirred in Et2O (40 mL) for 45 min. The resulting solid was filtered off and washed with Et2O (3.x.10 mL) to afford the HCl salt as a yellow solid (3.14 g). The crude salt was suspended in 1.0 N NaOH (100 mL) and stirred at 25° C. for 2 h. The solids were filtered, washed with water (2.x.10 mL), and dried to afford 2,4-Diamino-5-iodopyrimidine as a brown powder (1.71 g, 80percent). An analytical sample was prepared by recrystallization from MeCN to give 2,4-Diamino-5-iodopyrimidine as colorless crystals: Rf=0.25 (9:1, CHCl3:MeOH); mp=212-214° C.; 1H NMR (DMSO-d6) δ 7.92 (s, 1H), 6.40 (s, 2H), 6.10 (s, 2H); 13C NMR (DMSO-d6) δ 162.8, 162.7, 162.0, 61.2; HREI[M+]235.9559 (calculated C4H5IN4: 235.9559); Anal. (C4H5IN4) C, H, N.
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 4, p. 275 - 291
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 940 - 950
[3] Patent: US2009/105287, 2009, A1, . Location in patent: Page/Page column 26
[4] Chemical Communications, 2015, vol. 51, # 32, p. 7043 - 7046
Historical Records

Related Functional Groups of
[ 156-81-0 ]

Amines

Chemical Structure| 1004-38-2

[ 1004-38-2 ]

2,4,6-Triaminopyrimidine

Similarity: 0.97

Chemical Structure| 591-54-8

[ 591-54-8 ]

4-Aminopyrimidine

Similarity: 0.89

Chemical Structure| 22404-42-8

[ 22404-42-8 ]

N2-Methylpyrimidine-2,4-diamine

Similarity: 0.88

Chemical Structure| 174500-31-3

[ 174500-31-3 ]

Pyrimidin-4-amine dihydrochloride

Similarity: 0.86

Chemical Structure| 2434-56-2

[ 2434-56-2 ]

4,6-Diaminopyrimidine

Similarity: 0.86

Related Parent Nucleus of
[ 156-81-0 ]

Pyrimidines

Chemical Structure| 1004-38-2

[ 1004-38-2 ]

2,4,6-Triaminopyrimidine

Similarity: 0.97

Chemical Structure| 591-54-8

[ 591-54-8 ]

4-Aminopyrimidine

Similarity: 0.89

Chemical Structure| 22404-42-8

[ 22404-42-8 ]

N2-Methylpyrimidine-2,4-diamine

Similarity: 0.88

Chemical Structure| 174500-31-3

[ 174500-31-3 ]

Pyrimidin-4-amine dihydrochloride

Similarity: 0.86

Chemical Structure| 2434-56-2

[ 2434-56-2 ]

4,6-Diaminopyrimidine

Similarity: 0.86