931-86-2

Basic information

• Product Name: 5-Azacytosine
• Synonyms: 5-triazin-2(1h)-one,4-amino-3;2-Amino-4-hydroxy-1,3,5-triazine;2-AMINO-4-HYDROXY-S-TRIAZINE;5-AZACYTOSINE;4-AMINO-1,3,5-TRIAZIN-2-ONE;4-AMINO-1,3,5-TRIAZINE-2[1H]-ONE;4-AMINO-S-TRIAZIN-2(1H)-ONE;5-Azacytosine,98%
• CAS NO: 931-86-2
• Molecular Formula: C₃H₄N₄O
• Molecular Weight: 112.09
• EINECS: 213-242-9
• Product Categories: Amino Acids;Heterocyclic Compounds;All Inhibitors;Pyrimidines;Bases & Related Reagents;Inhibitors;Nucleotides;Pyrimidine purine
• Mol File: 931-86-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 209.98°C (rough estimate)
• Flash Point: 258.1 °C
• Appearance: crystalline solid
• Density: 1.86
• Refractive Index: 1.8010 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Aqueous Base (Slightly, Heated), DMSO (Slightly, Heated)
• PKA: 7.61±0.10(Predicted)
• BRN: 116378
• CAS DataBase Reference: 5-Azacytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Azacytosine(931-86-2)
• EPA Substance Registry System: 5-Azacytosine(931-86-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: XZ2854300
• Hazardous Substances Data: 931-86-2(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 931-86-2 differently. You can refer to the following data:
1. Used as the most effective cytosine mimics for the design of novel antiviral and anti-tumor drug candidates.
2. 5-Azacytosine can inhibits the growth of Escherichia coli and used as the most effective cytosine mimics for the design of novel antiviral and anti-tumor drug candidates.
3. Reactant for:Enzymic synthesis of nucleoside analogs using immobilized 2′-deoxyribosyltransferase from Lactobacillus reuteriReactions with oxide radical ionPotential antitumor and antiproliferative agent against human leukemia cells

Definition

ChEBI: A monoamino-1,3,5-triazine that is cytosine in which the aromatic CH at position 5 is replaced by a nitrogen.

InChI:InChI=1/C3H6N4O/c4-2-5-1-6-3(8)7-2/h1,3,8H,(H3,4,5,6,7)

Synthetic route

guanylurea formate (10043-39-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 5-azacytosine (931-86-2)

Conditions	Yield
With sodium methylate In methanol at 40 - 50℃; for 4h; Large scale;	90%
Stage #1: guanylurea formate With sodium methylate In methanol at 25 - 35℃; for 0.0833333h; Stage #2: N,N-dimethyl-formamide dimethyl acetal In methanol at 28 - 50℃;

formic acid (64-18-6) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 5-azacytosine (931-86-2)

Conditions	Yield
Stage #1: formic acid; N-Cyanoguanidine With toluene-4-sulfonic acid at 110℃; Autoclave; Large scale; Stage #2: With hydrogenchloride In water for 0.5h; Temperature; Reagent/catalyst; Reflux; Large scale;	85%

propyl methanoate (110-74-7) + N-cyanoacetamidine (56563-07-6) → 5-azacytosine (931-86-2)

Conditions	Yield
at 115℃; for 2h;	80%

N-cyanoacetamidine (56563-07-6) + formic acid ethyl ester (109-94-4) → 5-azacytosine (931-86-2)

Conditions	Yield
at 115℃; for 2h;	75%

Methyl formate (107-31-3) + N-cyanoacetamidine (56563-07-6) → 5-azacytosine (931-86-2)

Conditions	Yield
at 115℃; for 2h; Temperature;	73%

4-amino-2-chloro-1,3,5-triazine (7709-13-9) → 5-azacytosine (931-86-2)

Conditions	Yield
In hydrogenchloride; methanol for 0.5h; Heating;

5-aza-2'-deoxycytidine (2353-33-5, 22432-95-7) → 5-azacytosine (931-86-2) + D-2-deoxyribose (452-51-7, 13046-70-3, 29780-54-9, 36792-87-7, 36792-88-8, 113890-35-0, 113890-38-3)

Conditions	Yield
With water at 20℃; Acidic aqueous solution;

carbamimidoylurea (141-83-3) + orthoformic acid triethyl ester (122-51-0) → 5-azacytosine (931-86-2)

Conditions	Yield
In N,N-dimethyl-formamide at 155℃; for 1.5h;

5-azacytosine (931-86-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0)

Conditions	Yield
With ammonium sulfate for 8h; Product distribution / selectivity; Reflux;	98%
at 145 - 150℃; for 20h; Concentration;	96%
With ammonium sulfate at 120 - 150℃;	95.7%

5-azacytosine (931-86-2) + (S)-tritylglycidol (129940-50-7) → 1-[(2S)-2-hydroxy-3-(triphenylmethoxy)propyl]-5-azacytosine (933460-54-9)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 120℃; for 10h;	83%
With sodium hydroxide In dimethyl sulfoxide at 120℃; for 10h;	83%

5-azacytosine (931-86-2) + 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose (13035-61-5, 23094-61-3, 28708-32-9, 39727-26-9, 42927-46-8, 50730-26-2, 56272-01-6, 61248-15-5, 61826-42-4, 61849-90-9, 69855-18-1, 69855-19-2, 79120-80-2, 79120-81-3, 86782-36-7, 86782-94-7, 105453-36-9, 144490-03-9, 43225-70-3) → 4-amino-1-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-1,3,5-triazin-2(1H)-one

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 60 - 85℃; for 2h; Stage #2: 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose With trifluorormethanesulfonic acid In acetonitrile at 85℃; for 1h;	75%

1,1,1-trifluoro-2,3-epoxypropane (359-41-1) + 5-azacytosine (931-86-2) → 4-amino-1-(3,3,3-trifluoro-2-hydroxypropyl)-1,3,5-triazin-2(1H)-one

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 105 - 120℃; for 18h;	73%

5-azacytosine (931-86-2) + 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6, 6974-32-9, 14215-97-5, 16162-35-9, 20822-87-1, 21138-42-1, 22249-15-6, 22249-17-8, 26287-72-9, 53403-35-3, 53403-36-4, 57236-69-8, 70832-64-3, 99395-04-7, 100101-51-7, 109668-83-9, 120019-54-7) → 1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-azacytosine (206269-45-6)

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 18h; Heating; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 5h;	70%

5-azacytosine (931-86-2) + (R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate (1160512-81-1) → 1-[(2S)-2-(diisopropoxyphosphoryl)methoxy-3-hydroxypropyl]-5-azacytosine + diisopropyl {[(1R)-2-[(4-amino-1,3,5-triazin-2-yl)oxy]-1-(hydroxymethyl)ethoxy]methyl}-phosphonate (1207842-50-9) + 3-[(2S)-2-(diisopropoxyphosphoryl)methoxy-3-hydroxypropyl]-5-azacytosine (1207842-49-6)

Conditions	Yield
Stage #1: 5-azacytosine With sodium methylate In methanol for 14h; Reflux; Stage #2: (R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; regioselective reaction;	A 62% B 8% C 14%

1,2,3,5-tetra-O-acetyl-3-C-ethynyl-D-ribo-pentofuranose (848644-37-1) + 5-azacytosine (931-86-2) → 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-5-azacytosine (848644-46-2)

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 50℃;	50%

5-azacytosine (931-86-2) + 4-methyl-1-phenyl-1H-pyrrol-2(3H)-one → 5-methyl-4-[(5-methyl-3-oxo-2-phenyl-2,4-dihydro-3H-pyrazol-4-yl)methylene]-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (61466-03-3)

Conditions	Yield
In butan-1-ol for 4h; Condensation; Heating;	45%

5-azacytosine (931-86-2) + 1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose (134700-26-8) → C22H24N4O3S (1161853-96-8)

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 80℃; Reflux; Stage #2: 1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose With trifluorormethanesulfonic acid In acetonitrile at 80℃;	44%

5-azacytosine (931-86-2) + (6aR,9aS)-2,2,4,4-tetraisopropyl-8-((4-(octyloxy)benzyl)thio)tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocine → 4-amino-1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1,3,5-triazin-2(1H)-one

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 21h; Inert atmosphere; Reflux; Stage #2: (6aR,9aS)-2,2,4,4-tetraisopropyl-8-((4-(octyloxy)benzyl)thio)tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocine With N-Bromosuccinimide In dichloromethane at 0℃; for 2h; Inert atmosphere;	41.7%

5-azacytosine (931-86-2) + 2,3-O,O-dibenzyl-4-(5,6-epoxy)-L-ascorbic acid (318239-79-1) → 4-amino-1-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl]-1H-[1,3,5]triazin-2-one (1313583-60-6)

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 3h; Inert atmosphere; Reflux; Stage #2: 2,3-O,O-dibenzyl-4-(5,6-epoxy)-L-ascorbic acid With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 55 - 70℃; for 12h; Inert atmosphere;	27.2%

5-azacytosine (931-86-2) + 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine (98495-56-8) → α-5',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-5-azacytidine (1163302-11-1) + β-5',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-5-azacytidine (117399-71-0)

Conditions	Yield
Stage #1: 5-azacytosine; 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 3h; Reflux; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane for 6h; Reflux; Inert atmosphere;	A n/a B 25%

5-azacytosine (931-86-2) + 1-O-acetyl-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-erythro-pentofuranose (457653-05-3) → 4-amino-1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1,3,5-triazin-2(1H)-one

Conditions	Yield
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile	25%

5-azacytosine (931-86-2) + 2-deoxy–α-D-ribose 1-phosphate (17039-17-7) → 5-aza-2'-deoxycytidine (2353-33-5, 22432-95-7)

Conditions	Yield
With Escherichia coli purine nucleoside phosphorylase In aq. buffer at 20℃; for 0.5h; pH=7; Enzymatic reaction;	15%

5-azacytosine (931-86-2) + 5',6'-di-O-acetyl-2',3'-di-O-benzyl-L-ascorbic acid (231619-90-2) → (Z)-4-amino-1-(2-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidene)ethyl)-1,3,5-triazin-2(1H)-one (1313583-54-8)

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Inert atmosphere; Reflux; Stage #2: 5',6'-di-O-acetyl-2',3'-di-O-benzyl-L-ascorbic acid With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 55 - 70℃; for 16h; Inert atmosphere;	3.06%

5-azacytosine (931-86-2) + 2-(acetoxymethoxy)-1,3-propanediyl dibenzoate (110874-22-1) → 4-Amino-1-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-1H-[1,3,5]triazin-2-one (82410-28-4)

Conditions	Yield
Yield given. Multistep reaction;

5-azacytosine (931-86-2) + 1-O-acetyl-2,3-di-O-benzoyl-4-thio-DL-erythrofuranoside → 1-(2,3-di-O-benzoyl-4-thio-β-DL-erythrofuranosyl)-5-azacytosine

Conditions	Yield
With ammonium sulfate; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane 1.) reflux, 3 h, 2.) CH2Cl2, r.t., 10 h; Yield given. Multistep reaction;

5-azacytosine (931-86-2) + 1-O-acetyl-4-(carboethoxy)-2,3-dideoxy-L-ribofuranose (208173-53-9) → (2R,5S)-5-(4-Amino-2-oxo-2H-[1,3,5]triazin-1-yl)-tetrahydro-furan-2-carboxylic acid ethyl ester + (2R,5R)-5-(4-Amino-2-oxo-2H-[1,3,5]triazin-1-yl)-tetrahydro-furan-2-carboxylic acid ethyl ester

Conditions	Yield
With 2,6-dimethylpyridine; trimethylsilyl iodide; t-butyldimethylsiyl triflate 1.) CH2Cl2; 2.) r.t.; Yield given. Multistep reaction. Yields of byproduct given;

5-azacytosine (931-86-2) + chloro-trimethyl-silane (75-77-4) + acetic anhydride (108-24-7) → N-(4-Trimethylsilanyloxy-[1,3,5]triazin-2-yl)-acetamide

Conditions	Yield
With triethylamine

5-azacytosine (931-86-2) + 1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose (169736-17-8) → 1-(2-deoxy-3,5-di-O-p-toluoyl-4-thio-β-D-erythropentofuranosyl)-5-azacytosine (676487-18-6) + 1-(2-deoxy-3,5-di-O-p-toluoyl-4-thio-α-D-erythropentofuranosyl)-5-azacytosine (676487-25-5)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate Substitution;
Stage #1: 5-azacytosine; 1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -78℃; for 2.5h;	A 100 mg B 200 mg

5-azacytosine (931-86-2) + 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose → 1-(2-deoxy-3,5-di-O-acetyl-4-thio-α-L-threopentofuranosyl)-5-azacytosine (676487-27-7) + 1-(2-deoxy-3,5-di-O-acetyl-4-thio-β-L-threopentofuranosyl)-5-azacytosine (676487-22-2)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate Substitution;
Stage #1: 5-azacytosine; 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -78℃; for 2h;	A 75 mg B 160 mg

5-azacytosine (931-86-2) + (2R)-2-benzyloxymethyl-4-acetoxy-1,3-dioxolane (307002-00-2) → 4-Amino-1-((2R,4S)-2-benzyloxymethyl-[1,3]dioxolan-4-yl)-1H-[1,3,5]triazin-2-one + 4-Amino-1-((2R,4R)-2-benzyloxymethyl-[1,3]dioxolan-4-yl)-1H-[1,3,5]triazin-2-one

Conditions	Yield
Stage #1: 5-azacytosine With 1,1,1,3,3,3-hexamethyl-disilazane for 4h; silylation; Heating; Stage #2: (2R)-2-benzyloxymethyl-4-acetoxy-1,3-dioxolane With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 18h; Condensation;

Upstream product

• 10043-39-7 guanylurea formate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 141-83-3 carbamimidoylurea 
• 122-51-0 orthoformic acid triethyl ester 
• 2353-33-5 5-aza-2'-deoxycytidine 
• 7709-13-9 4-amino-2-chloro-1,3,5-triazine 
• 64-18-6 formic acid 
• 127099-85-8 N-Cyanoguanidine 
• 110-74-7 propyl methanoate 
• 56563-07-6 N-cyanoacetamidine 
• 109-94-4 formic acid ethyl ester 
• 107-31-3 Methyl formate 

Downstream Products

• 52523-35-0 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine 
• 1161853-96-8 C₂₂H₂₄N₄O₃S 
• 2353-33-5 5-aza-2'-deoxycytidine 
• 320-67-2 5-azacytidine 
• 1313583-60-6 4-amino-1-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl]-1H-[1,3,5]triazin-2-one 
• 1313583-54-8 (Z)-4-amino-1-(2-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidene)ethyl)-1,3,5-triazin-2(1H)-one 
• 933460-54-9 1-[(2S)-2-hydroxy-3-(triphenylmethoxy)propyl]-5-azacytosine 
• 4040-08-8 N-butyl-[1,3,5]triazine-2,4-diamine 
• 61466-03-3 5-methyl-4-[(5-methyl-3-oxo-2-phenyl-2,4-dihydro-3H-pyrazol-4-yl)methylene]-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 
• 324018-61-3 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-azacytosine 
• 206269-45-6 1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-azacytosine 

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