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Product Details of [ 56-06-4 ]

CAS No. :56-06-4 MDL No. :MFCD08528919
Formula : C4H6N4O Boiling Point : -
Linear Structure Formula :- InChI Key :SWELIMKTDYHAOY-UHFFFAOYSA-N
M.W : 126.12 Pubchem ID :135408763
Synonyms :
DAHP
Chemical Name :2,6-Diaminopyrimidin-4(1H)-one

Calculated chemistry of [ 56-06-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 33.67
TPSA : 97.79 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) : -8.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.2
Log Po/w (XLOGP3) : -1.77
Log Po/w (WLOGP) : -1.05
Log Po/w (MLOGP) : -1.01
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : -0.85

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.0
Solubility : 126.0 mg/ml ; 1.0 mol/l
Class : Very soluble
Log S (Ali) : 0.23
Solubility : 215.0 mg/ml ; 1.71 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.8
Solubility : 20.0 mg/ml ; 0.158 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 56-06-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 56-06-4 ]

* 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.

  • Upstream synthesis route of [ 56-06-4 ]
  • Downstream synthetic route of [ 56-06-4 ]

[ 56-06-4 ] Synthesis Path-Upstream   1~26

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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 2
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  • [ 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
  • [ 77287-34-4 ]
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  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
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  • [ 56-06-4 ]
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  • [ 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
  • 4
  • [ 77287-34-4 ]
  • [ 23147-58-2 ]
  • [ 1455-77-2 ]
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  • [ 328-42-7 ]
  • [ 110-15-6 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 57-13-6 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 5
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  • [ 57-13-6 ]
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Patent: US5698695, 1997, A,
  • 7
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YieldReaction ConditionsOperation in experiment
85% at 97℃; for 17 h; 2,4-Diamino-6-hydroxypyrimidine (1) (1.00 g, 7.93 mmol) wasadded to POCl3 (9 mL), and stirred at 97 C for 17 h. The reaction solution was added to ice waterslowly, and then stirred at 90 C for 1 h. The pH of this solution was adjusted to 8 with NaOH,and then it was extracted with EtOAC (150 mL 3). The combined organic layers were dried withNa2SO4, filtered and concentrated to give white solid 0.97 g, yield 85percent. m.p. 200.2–200.4 C; IR(KBr): max/cm-1 3449 (NH), 3327 (NH), 1642 (C=N), 1581 (C=C), 1551 (C=C), 795 (C-Cl); 1H-NMR(DMSO-d6) δ6.57 (s, 2H, NH2), 6.31 (s, 2H, NH2), 5.69 (s, 1H, Ar-H); ES-MS 145.0 (M + H)+; HRMSCalcd. for C16H20ClN4O3+ 145.0281, found 145.0276.
Reference: [1] Molecules, 2017, vol. 22, # 10,
  • 8
  • [ 14989-30-1 ]
  • [ 56-06-4 ]
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YieldReaction ConditionsOperation in experiment
47.3% With sodium hydroxide; potassium carbonate; trichlorophosphate In tetrahydrofuran; water; acetone b)
Preparation of 6-chloro-2,4-diaminopyrimidine
In a 200 l multi-purpose glass lined reactor, connected to a sodium hydroxide trap, phosphorous oxychloride (88 l = 147 kg) and 2,6-diamino-4-hydroxypyrimidine (22.2 kg) were charged.
The suspension was heated to reflux under stirring for 5 hours, then part of the oxychloride (22 l) was distilled at room pressure.
The residue was cooled and left to stand overnight, then heated to pre-fluidize the viscous oil, which was charged into a flask provided with a blowdown valve on the bottom.
The flask was transferred over a 1000 l glass lined reactor containg 290 l of water.
The heated oil was added under stirring, adjusting cooling so that temperature approached as much as possible to 100°C around the end of the addition.
At the end of the addition, the solution was refluxed for 10 min., cooled and added with 230 kg of potassium carbonate to a pH from 8.5 to 9.0, under suction.
The solid was centrifuged without washing the cake, granulated and dried in oven at 70°C.
The dried solid was kneaded at ebollition for 2 hours in 100 l of tetrahydrofuran, the suspension was cooled to room temperature and filtered on a filter press, on which a celite or charcoal layer had been previously placed.
The pressed solid was then discharged into the reactor and subjected to the same treatment.
The collected filtrates were concentrated to dryness at room pressure and the residual solid was kneaded at ebollition for 30 min. in 25 l of acetone, the suspension was cooled and pump-filtered, and dried first in the air, then in oven at 70°C.
11.9 kg (yield 47.3percent) of a light cream solid was obtained, unitary in T.L.C. (CHCl35/MeOH 4/AcOEt 1): Rf 0.6; melting at 197-199°C.
Reference: [1] Patent: EP295218, 1988, A1,
  • 9
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YieldReaction ConditionsOperation in experiment
64%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5 h; Inert atmosphere
174 mg of sodium hydride (60percent in mineral oil, 4.36 mmol) are added in portions under an argon atmosphere to a vigorously stirred solution of 500 mg (3.96 mmol) of 2,6-diaminopyrimidin-4-ol in 10 ml of DMF. After 30 min, 700 μl (5.15 mmol) of ethyl trifluoromethanesulfonate are added dropwise, and the solution is stirred for a further 20 min.
Methanol (1 ml) is then added to the reaction mixture, which is directly purified by preparative HPLC.
Combining the product fractions and removing the solvent result in 370 mg (64percent of theory) of the title compound as a white solid.
LC-MS (method 5): Rt=2.24 min; MS (ESIpos): m/z=155 [M+H]+
1H-NMR (400 MHz, DMSO-d6): δ=1.21 (t, 3H), 4.12 (q, 2H), 5.00 (s, 1H), 5.87 (s, 2H), 6.01 (s, 2H).
Reference: [1] Patent: US2010/35902, 2010, A1, . Location in patent: Page/Page column 20
  • 10
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YieldReaction ConditionsOperation in experiment
56% With sodium acetate In water at 65℃; for 3.5 h; Example 1Step Al:2-Amino-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one. To a mixture of 2,4-diamino-6- hydroxypyrimidine (20.0 g, 159 mmol) and NaOAc (26.0 g, 317 mmol) in H2O (300 mL) at 650C was added a solution of chloroacetaldehyde (22.0 mL, 50percent in H2O, 173 mmol) in H2O (22 mL) dropwise for 90 min. The mixture was stirred at 650C for an additional 2 h and cooled to room temperature. The reaction mixture was concentrated in vacuo to one third of its original volume and stored at 4 0C for 16 h. The light pink precipitates were filtered, washed with an ice cold H2O (5 mL), and dried under high vacuum for 16 h. The precipitates were placed in Soxhlet extractor and refluxed with methanol (200 mL) for 24 h. The methanol was concentrated to give 13.3 g (56percent) of 2-amino-3,7-dihydro-pyrrolo[2,3- d]pyrimidin-4-one as a light pink solid.
52% With sodium acetate In water; N,N-dimethyl-formamide at 20℃; for 48 h; Step 1.
2-Amino-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one
A mixture of 2,4-diamino-6-hydroxypyrimidine (300 g, 2.37 mol), chloroacetaldehyde (50percent aq. solution, 382 g, 2.43 mol, 303 mL, 1.02 eq.), sodium acetate (195 g, 2.37 mol), DMF (2.5 L), and water (360 mL) was stirred mechanically at rt for 2 days.
The resulting solid was collected by filtration, and washed with water (50 mL*3).
The mother liquor was concentrated to give additional material which was washed with water (50 mL*3).
The combined solid materials were recrystallized from MeOH to give the title compound as a white powder (186 g, 52percent yield, HPLC purity: 100percent).
tR: 2.21 min. 1H-NMR (DMSO-d6) δ 11.00 (br. s, 1H), 10.33 (br. s, 1H), 6.63 (q, 1H), 6.21 (q, 1H), 6.12 (br. s, 2H).
23% With sodium acetate In water at 80℃; 2,4-diamino-6-hydroxypyrimidine (3.02 g, 23.6 mmol) was dissolved in water (60 mL) containing sodium acetate (1.97 g, 24.0 mmol). The solution was heated to 80 °C until a clear solution was obtained. Then 50percent aq. alpha-chloroacetaldehyde (2.52 mL, 39.0 mmol) was introduced and the solution was left stirring at 80°C overnight. A brown precipitate was recovered, dried and purified by flash chromatography using CHCl3/MeOH (0.80 g, 5.33 mmol, 23percent). 1H NMR (500 MHz, DMSO-d6) δH (ppm): 10.94 (s, 1H, NH-9), 10.19 (s, 1H, NH-1), 6.61 (d, 1H, J=2.20 Hz, H-8), 6.19 (d, 1H, J=2.15 Hz, H-7), 6.01 (s, 2H, NH2-2). 13C NMR (126 MHz, DMSO-d6) δC (ppm): 158.83 (s, C=O), 152.17 (s, C-2), 151.12 (s, C-4), 116.55 (s, C-8), 101.55 (s, C-7), 99.84 (s, C-5).
19 g
Stage #1: With sodium acetate In water; N,N-dimethyl-formamide for 1 h;
Stage #2: at 20℃; for 48 h;
Step 1. Creation of the heterocycle (FIG. 3). To a solution of 2,4-diamino-6-hydroxypyrimidine (1, 25.2 g) in DMF (480 mL) and water (80 mL) was added sodium acetate (27.2 g). The resulting yellow solution was stirred for 1 h. To the solution was added chloroacetaldehyde (50percent solution, 25.4 mL) and the mixture was stirred at rt for 2 days. The volatiles were removed in vacuo and the residue was mixed with methanol (70 mL) and stored at rt overnight. The resulting solid was filtered. The solid was mixed with methanol (150 mL) and heated at 60° C. for 10 min and cooled to rt overnight. The resulting solid was filtered and dried. The yield of 2 was 15 g to 19 g. (0032) A mixture of 7-deazaguanine (14.2 g) and dimethylaniline (6 mL) in POCl3 (200 mL) was refluxed for 3 h (bath temp. 130° C.). After cooling to rt, volatiles were removed by distillation (bath temp 60° C.). The residue was mixed with water (2300 mL) and neutralized with ammonium hydroxide until complete precipitation of solid (pH4). The resulting precipitate was filtered and further purified by column chromatography (silica, MC:MeOH=10:1) to give 3.6 g (21.4 mmol, 23percent) of solid (FIG. 3).

Reference: [1] Angewandte Chemie - International Edition, 2007, vol. 46, # 13, p. 2325 - 2327
[2] Bioorganic Chemistry, 2001, vol. 29, # 1, p. 36 - 55
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 90 - 98
[4] Patent: WO2006/122003, 2006, A2, . Location in patent: Page/Page column 13
[5] Patent: US2006/223797, 2006, A1, . Location in patent: Page/Page column 83-84
[6] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1124 - 1129
[7] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 2260 - 2264
[8] Patent: WO2012/45195, 2012, A1, . Location in patent: Page/Page column 59
[9] Patent: WO2012/74999, 2012, A1, . Location in patent: Page/Page column 125; 126
[10] Patent: US10059735, 2018, B1, . Location in patent: Page/Page column 4; 5
  • 11
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YieldReaction ConditionsOperation in experiment
20%
Stage #1: With sodium acetate In water at 60℃; for 0.25 h;
Stage #2: at 60℃; for 2 h;
Synthesis of Compound (37)Intermediate AA (0.5g, 3.96 mmol) was added to a solution of NaOAc (0.647g, 4.76 mmol, 1.2 eq.) in H20 (15 mL). The reaction was heated to 60 °C for ~15 minutes, and a solution of 50percent aqueous ClCH2CHO (0.5 mL) was then added. The reaction stirred for 2 hours at 60 °C. The reaction mixture was filtered to remove undissolved material, and the filtrate stored at 0 °C overnight. The resulting precipitated solid was collected by filtration, washed with cold H20, and dried to obtain Compound (37) (120mg, 20percent) as a pink solid. Rf = 0.7 (30percentMeOH/CHCl3/0.2 mL of aqueous NH3). 1H-NMR (400MHz, DMSO-_3/4 δ 10.95 (br. s, exchanged with D20, 1H), 10.20 (s, exchanged with D20, 1H), 6.60 (dd, J = 3.2, 2.0Hz, 1H), 6.18 (dd, J = 3.2, 2.0Hz, 1H), 6.03 (br. s, exchanged with D20, 2H). Mass (m/z): 150.8 (M++l). LCMS: (Column: Zodiacsil 120-5-C-18-Aq (4.6 * 50 mm), Mobile phase: A: 0.01M HCOONH4 (Aq); B: MeOH, T/percentB: 0/5, 10/90, 10.1/5, Flow: 1.0 mL/min, Diluent: MeOH), Rt=2.599 min, 99.16 (214 nm), 99.10 (254 nm).
Reference: [1] Patent: WO2011/35009, 2011, A1, . Location in patent: Page/Page column 74
  • 12
  • [ 506-93-4 ]
  • [ 105-56-6 ]
  • [ 56-06-4 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium methylate In methanol for 4 h; Reflux
Stage #2: With hydrogenchloride In water
In a four-necked flask, 300 ml of methanol, 110 g of guanidine nitrate, and 55 g of sodium methoxide were heated and stirred for 1 hour.In the reflux state, methyl cyanoacetate was added dropwise. After refluxing for 4 hours, the recovered methanol was distilled off (applied), 800 ml of water was added, and the pH was adjusted to 9 with hydrochloric acid.Then, 50percent of acetic acid was used to adjust pH=7, cooled to 5-10° C., filtered, washed with water and dried to obtain 120 g of DAHP dry product with a yield of 95percent and a content of 99.1percent.
Reference: [1] Patent: CN107857734, 2018, A, . Location in patent: Paragraph 0032; 0033; 0034; 0035
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  • [ 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
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  • [ 77287-34-4 ]
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  • [ 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
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  • [ 88075-70-1 ]
  • [ 56-06-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, # 6, p. 1697 - 1700
  • 16
  • [ 108-98-5 ]
  • [ 100061-59-4 ]
  • [ 831-91-4 ]
  • [ 56-06-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 503 - 508
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Reference: [1] Russian Journal of General Chemistry, 1997, vol. 67, # 3, p. 435 - 438
  • 18
  • [ 506-93-4 ]
  • [ 105-34-0 ]
  • [ 56-06-4 ]
Reference: [1] Patent: CN104109163, 2016, B, . Location in patent: Paragraph 0017
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  • [ 23147-58-2 ]
  • [ 1455-77-2 ]
  • [ 849585-22-4 ]
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  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 57-13-6 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
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  • [ 328-42-7 ]
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  • [ 110-15-6 ]
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  • [ 120-73-0 ]
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  • [ 57-13-6 ]
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  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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  • [ 51953-18-5 ]
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  • [ 127-17-3 ]
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  • [ 18514-52-8 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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  • [ 3346-23-4 ]
YieldReaction ConditionsOperation in experiment
96.4% at 30 - 35℃; for 2 h; Dissolve 126 g of diaminopyrimidine730 g of the above batch of filtrate, stirring, temperature control 30 ~ 35 °C,Add 20g of concentrated sulfuric acid,The mass concentration is 98percent.After the dropwise addition, 68.5 g (1.01 mol) of 93percent fuming nitric acid was continuously added dropwise at 30 to 35°C.After dripping, continue the incubation for 2 hours.After the reaction is completed, cool and crystallize to -5~0°C and filter.About 730 g of brownish red filtrate was obtained as the next batch of reaction solvent.The cake was washed with 100 mL of dichloromethane,200mL drinking water washing, draining,225 g (of 165 g) was obtained as a tan-yellow-brown red solid, i.e. a nitropyrimidine (MW 171.11) wet product.HPLC purity 98.7percent, measured as diaminopyrimidine,The yield was 96.4percent.
Reference: [1] Patent: CN107903215, 2018, A, . Location in patent: Paragraph 0039-0050
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  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
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  • [ 328-42-7 ]
  • [ 2491-15-8 ]
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  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
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  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 24
  • [ 53106-70-0 ]
  • [ 56-06-4 ]
  • [ 69205-79-4 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With sodium acetate In water at 50℃; for 1 h;
Stage #2: at 50 - 100℃; for 21 h;
Preparation 4: 2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine- 5-carbonitrile 2,4-Diamino-6-hydroxypyrimidine (3.00 g, 24 mmol) was added to a solution of sodium acetate (6.4g, 76 mmol) in millipore water (90 mL) and stirred at 50 °C for 1 hour. While still at 50 °C a solution of crude chloro(formyl)acetonitrile (3.00 g,32 mmol) in mQ water (44 mL) was added dropwise with a dropping funnel, during which time the reaction turned beigeand heating continued for 18 h at 50 °C, after which time the reaction was heated to 100 °C for 3 h. The reaction mixture was allowed to cool to room temperature and the solid removed by filtration. The solid was suspended in EtOH and SM aqueous KOH solution was added until the soliddissolved. Charcoal was added to the solution and the mixture stirred for 30 minutes before removal of the solid by filtration. The pH of the filtrate was adjusted to pH=6 with concentrated aqueous HCI solution during which time a precipitate formed and was collected by filtration. In order to remove the final traces of water from the solid it was dissolved in a mixture of toluene/methanol 1/1 and thenconcentrated at reduced pressure. The resultant solid was dried over P205 to afford the desired compound (1.68 g, 9.6 mmol, 40percent yield) as beige solid. Procedure based on Brooks 2012.OH (400 MHz, DMSO-d6) 0 11.98 (br s, 1H) 10.74 (br s, 1H), 7.59 (s, 1H), 6.43 (s, 2H).Oc(100 MHz, DMSO-d6) 0 158.0, 154.3, 152.1, 128.2, 116.4, 99.2, 86.0. HRMS (m/z ESI): C7H5N50 EM-H]- Found 174.0415 Requires: 174.0416.
1.68 g With sodium acetate In water at 50 - 100℃; for 22 h; 2,4-Diamino-6-hydroxypyrimidine (3.00 g, 24 mmol) was added to a solution of sodium acetate (6.4g, 76 mmol) in millipore water (90 ml.) and stirred at 50 °C for 1 hour. While still at 50 °C a solution of crude chloro(formyl)acetonitrile (3.00 g, 32 mmol) in mQ water (44 ml.) was added dropwise with a dropping funnel, during which time the reaction turned beige and heating continued for 18 h at 50 °C, after which time the reaction was heated to 100 °C for 3 h. The reaction mixture was allowed to cool to room temperature and the solid removed by filtration. The solid was suspended in EtOH and 5M aqueous KOH solution was added until the solid dissolved. Charcoal was added to the solution and the mixture stirred for 30 minutes before removal of the solid by filtration. The pH of the filtrate was adjusted to pH=6 with concentrated aqueous HCI solution during which time a precipitate formed and was collected by filtration. In order to remove the final traces of water from the solid it was dissolved in a mixture of toluene/methanol 1/1 and then concentrated at reduced pressure. The resultant solid was dried over P2O5 to afford the desired compound (1.68 g, 9.6 mmol, 40percent yield) as beige solid. Procedure based on Brooks 2012. δΗ (400 MHz, DMSO-tfe) δ 11.98 (br s, 1H) 10.74 (br s, 1H), 7.59 (s, 1H), 6.43 (s, 2H). δα (100 MHz, DMSO-tfe) δ 158.0, 154.3, 152.1, 128.2, 116.4, 99.2, 86.0. HRMS (m/z ESI ) : C7H5N5O [M-H]" Found 174.0415 Requires: 174.0416.
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 32, p. 5747 - 5750
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 11-12, p. 2191 - 2198
[3] Patent: WO2016/50806, 2016, A1, . Location in patent: Page/Page column 22; 23
[4] Patent: WO2016/50804, 2016, A1, . Location in patent: Page/Page column 20
  • 25
  • [ 107-31-3 ]
  • [ 56-06-4 ]
  • [ 107-14-2 ]
  • [ 69205-79-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 23, p. 3821 - 3825
  • 26
  • [ 56-06-4 ]
  • [ 157848-19-6 ]
  • [ 155405-80-4 ]
Reference: [1] Patent: WO2011/64256, 2011, A1, . Location in patent: Page/Page column 16-17
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