71-30-7

Basic information

• Product Name: Cytosine
• Synonyms: 4-AMINO-2(1H)-PYRIMIDINONE;4-AMINO-2(1)-PYRIMIDONE;4-AMINO-2-PYRIMIDINOL;4-AMINO-2-OXO-1,2-DIHYDROPYRIMIDINE;4-AMINO-2-HYDROXYPYRIMIDINE;2-Oxy-4-amino pyrimidine;AURORA KA-682;CYTOSINE
• CAS NO: 71-30-7
• Molecular Formula: C₄H₅N₃O
• Molecular Weight: 111.1
• EINECS: 200-749-5
• Product Categories: Pharmaceutical Intermediates;PYRIMIDINE;FINE Chemical & INTERMEDIATES;Pyridines, Pyrimidines, Purines and Pteredines;Pyrimidine series;Nucleotides and Nucleosides;Cidofovir;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides;Building Blocks;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks;Pyrimidines;amine |ketone;nucleoside
• Mol File: 71-30-7.mol
• Article Data: 75

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 208.2°C (rough estimate)
• Flash Point: 223.4 °C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 0,48 g/cm3
• Vapor Pressure: 1.46E-08mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Clear to very slightly hazy colorless to faint yellow solution a
• PKA: 4.60, 12.16(at 25℃)
• Water Solubility: soluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,2795
• BRN: 2637
• CAS DataBase Reference: Cytosine(CAS DataBase Reference)
• NIST Chemistry Reference: Cytosine(71-30-7)
• EPA Substance Registry System: Cytosine(71-30-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• RTECS: UW7350150
• TSCA: Yes
• Hazardous Substances Data: 71-30-7(Hazardous Substances Data)

Usage

Description

Cytosine is pyrimidine; along with adenine and guanine they account for the fi ve nucleic acid bases. Pyrimidines are heterocyclic single-ringed compounds based on the structure of pyrimidine. Cytosinelike adenine and guanine, form nucleosides and nucleotides in RNA and DNA. When the bases combine with ribose, a ribonucleoside forms; and when it attaches to deoxyribose, a deoxyribosenucleoside is formed. Names of the nucleoside are summarized in Table 29.1.these in turn combine with phosphoryl groups, in a process called phosphorylation, to form their respective nucleotides that form nucleic acids.the nucleotides can be tri, di, and mono phosphate nucleotides similar to the way in which adenine forms ATP, ADP, and AMP.

Chemical Properties

White Solid

History

Cytosine is first isolated by hydrolysis of calf thymus tissue by Albrecht Kossel (1853–1927) and A. Neumann during 1893–1894. Thymine’s structure was published in 1900 and confi rmed over the next several years when it was synthesized by several investigators. In 1903, cytosine was synthesized by Henry Lord Wheeler (1867–1914) and Treat B. Johnson, confirming its structure. Uracil was first isolated in 1900 from yeast nucleic acid found in bovine thymus and herring sperm.the methylation of uracil produces thymine; thymine is also called 5-methyluracil because methylation takes place at the fi fth carbon in uracil to produce thymine.

Uses

Different sources of media describe the Uses of 71-30-7 differently. You can refer to the following data:
1. Cytosine is a nucleoside used for proteomics research. It is also used as an enzyme substrate or precursor of effector molecules such as cytosine sugars.
2. Cytosine has been used: for the preparation of nucleobase solutions as a standard for high-performance liquid chromatography (HPLC)for the estimation of global methylation ratefor nucleoside 5′-triphosphate (NTP) synthesis purification

Definition

Different sources of media describe the Definition of 71-30-7 differently. You can refer to the following data:
1. ChEBI: An aminopyrimidine that is pyrimidin-2-one having the amino group located at position 4.
2. A nitrogenous base found in DNA and RNA. Cytosine has the pyrimidine ring structure.
3. cytosine: A pyrimidine derivative.It is one of the principal componentbases of nucleotides and the nucleicacids DNA and RNA.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Biochem/physiol Actions

Cytosine (C) is one of the four main bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA).

Purification Methods

Cytosine crystallises from H2O as the monohydrate which loses water on heating above 100o. Its solubility in H2O is 0.77%. UV: max 267nm ( 6,100) in H2O pH 8.8 and 275nm ( 10,400) in 0.1N HCl. [Hilbert & Johnson J Am Chem Soc 52 1152 1930, Hilbert et al. J Am Chem Soc 57 552 1935, Beistein 25 III/IV 3654.]

InChI:InChI=1/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)

Synthetic route

C-(6-Methoxy-2-p-tolyl-quinolin-4-yl)-N-(2-oxo-1,2-dihydro-pyrimidin-4-yl)-methanesulfonamide → 6-methoxy-2-(p-tolyl)quinoline (117839-37-9) + Cytosine (71-30-7) + 6-methoxy-4-methyl-2-(p-tolyl)quinoline (117839-39-1)

Conditions	Yield
In isopropyl alcohol Irradiation; 350 nm;	A n/a B 94% C n/a

2-thiocytosine (333-49-3) → Cytosine (71-30-7)

Conditions	Yield
With dihydrogen peroxide at 80℃; for 20h; Temperature;	93%

3-hydroxylacrylic nitrile (25078-62-0) + urea (57-13-6) → Cytosine (71-30-7)

Conditions	Yield
Stage #1: 3-hydroxylacrylic nitrile With sodium t-butanolate In tert-butyl alcohol Stage #2: urea In tert-butyl alcohol at 50℃; for 8h; Solvent; Reagent/catalyst; Temperature;	91.5%

urea, monosodium salt (29878-39-5) + 3-hydroxylacrylic nitrile (25078-62-0) → Cytosine (71-30-7)

Conditions	Yield
Stage #1: 3-hydroxylacrylic nitrile With sodium methylate In methanol Stage #2: urea, monosodium salt In methanol at 40℃; for 6h;	91.5%

urea, monopotassium salt (89186-10-7) + 3-hydroxylacrylic nitrile (25078-62-0) → Cytosine (71-30-7)

Conditions	Yield
Stage #1: 3-hydroxylacrylic nitrile With sodium methylate In methanol Stage #2: urea, monopotassium salt In methanol at 40℃; for 6h;	91.5%

4-amino-2-methoxypyrimidine (3289-47-2) → Cytosine (71-30-7)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 1h; Temperature;	91.2%
With hydrogenchloride; water

4-amino-2-(methylthio)pyrimidine (2183-66-6) → Cytosine (71-30-7)

Conditions	Yield
With hydrogenchloride; water at 90℃; for 1h;	90.9%

2-benzylsulfanyl-pyrimidin-4-ylamine (60722-70-5) → Cytosine (71-30-7)

Conditions	Yield
With hydrogenchloride; water at 90℃; for 1h;	90.6%

2-ethylsulfanyl-pyrimidin-4-ylamine (54308-63-3) → Cytosine (71-30-7)

Conditions	Yield
With hydrogenchloride; water at 90℃; for 1h;	89.7%
With ethanol; water; dihydrogen peroxide

3,3-diethoxypropenenitrile (35146-02-2) + urea (57-13-6) → Cytosine (71-30-7)

Conditions	Yield
With sodium hydroxide In toluene for 12h; Reflux;	89%

5-carboxylcytosine (3650-93-9) → Cytosine (71-30-7)

Conditions	Yield
With ammonium chloride In 1-methyl-pyrrolidin-2-one at 180℃; for 8h; Reagent/catalyst; Temperature; Solvent;	87%

3-hydroxyacrylonitrile sodium salt (76064-23-8) + urea (57-13-6) → Cytosine (71-30-7)

Conditions	Yield
In toluene for 5h;	84%

sodium cyanamide (19981-17-0, 20611-81-8, 123092-13-7, 17292-62-5) + N4-<(Dimethylamino)methylene>cytosine (76299-81-5) → Cytosine (71-30-7) + <(Dimethylamino)methylene>cyanamide (39687-97-3)

Conditions	Yield
In isopropyl alcohol for 2h; Heating;	A n/a B 81%

N4-<(Dimethylamino)methylene>cytosine (76299-81-5) → Cytosine (71-30-7) + <(Dimethylamino)methylene>cyanamide (39687-97-3)

Conditions	Yield
With sodium cyanamide In isopropyl alcohol for 2h; Heating;	A n/a B 81%

4-methylsulfanylpyrimidin-2(1H)-one (35551-31-6) → Cytosine (71-30-7)

Conditions	Yield
With ferrous(II) sulfate heptahydrate; ammonium hydroxide at 80℃; for 72h;	77%

4-(benzoylamino)-1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-1H-pyrimidin-2-one (1257309-82-2) → N-(1,3-propanediol-2-yl)acetamide (2655-79-0) + Cytosine (71-30-7)

Conditions	Yield
With ammonium hydroxide; water In methanol at 70℃; for 24h; Sealed tube;	A 71% B 75%

C5H6N2O2 → Cytosine (71-30-7)

Conditions	Yield
With ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; under 11251.1 Torr; for 20h; Autoclave;	74%

N4-<(Dimethylamino)methylene>cytosine (76299-81-5) → Cytosine (71-30-7) + N-[6-Oxo-6,7-dihydro-pyrimido[1,6-a][1,3,5]triazin-(4E)-ylidene]-guanidine; hydrochloride (76299-79-1)

Conditions	Yield
With guanidine hydrochloride In isopropyl alcohol for 17h; Heating;	A 67% B 8%

2'-Deoxycytidine (951-77-9) → Cytosine (71-30-7)

Conditions	Yield
With purine nucleoside phosphorylase at 14 - 15℃; pH=7; aq. phosphate buffer; Enzymatic reaction;	60%
	4 % Chromat.

4-(benzoylamino)-1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-1H-pyrimidin-2-one (1257309-82-2) → N-(1,3-propanediol-2-yl)acetamide (2655-79-0) + 4-amino-1-{N-[1-hydroxy-3-(pivaloyloxymethyl)prop-2-yl]acetylaminomethyl}-1H-pyrimidin-2-one + 4-(amino)-1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-1H-pyrimidin-2-one + Cytosine (71-30-7)

Conditions	Yield
With ammonium hydroxide; water In methanol at 20℃; for 24h;	A 58% B 4% C 12% D 60%

CYTIDINE (65-46-3) → Cytosine (71-30-7) + uracil (66-22-8)

Conditions	Yield
With sodium persulfate In water at 75℃; for 4h; sodium phosphate buffer pH 7.0, other substrates;	A 53% B 6%

methanol (67-56-1) + Flucytosine (2022-85-7) → 5-methoxycytosine (31458-47-6) + Cytosine (71-30-7) + 6-methoxycytosine

Conditions	Yield
for 3h; Mechanism; Product distribution; Irradiation; other alcohol;	A 36% B 9% C 31%
for 3h; Irradiation;	A 36% B 9% C 31%

1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine hydrochloride (134665-72-8) → Cytosine (71-30-7) + 1,4-anhydro-2-C-cyano-2-deoxy-D-erythropent-1-enitol + 2'-C-cyano-2'-deoxy-1-β-D-ribo-pentofuranosylcytosine

Conditions	Yield
With Tris-HCl buffer at 37℃; for 6h; Rate constant; Mechanism; var. salt concentration and pH of buffer;	A n/a B 28% C 33%

α-cytidine-5′-phosphate → Cytosine (71-30-7) + C9H12N3O7P(2-) + C9H11N2O8P(2-) + C6H8NO7P(2-) + C9H12N3O7P(2-) + C9H11N2O8P(2-) + uracil (66-22-8) + C9H11N2O8P(2-)

Conditions	Yield
In water at 90℃; for 16h; pH=6.5; Irradiation; Inert atmosphere;	A 12% B 5% C 11% D 22% E 5% F 9% G 14% H 5%

...Expand

2-chloropyrimidin-4-amine (7461-50-9) → Cytosine (71-30-7)

Conditions	Yield
With hydrogenchloride; water

4-ethoxypyrimidin-2-one (6220-43-5) → Cytosine (71-30-7)

Conditions	Yield
With ethanol; ammonia at 120℃;

(4-amino-pyrimidin-2-ylsulfanyl)-acetic acid (61445-73-6) → Cytosine (71-30-7)

Conditions	Yield
With hydrogenchloride; water

cytidinium sulphate (32747-18-5) → Cytosine (71-30-7)

Conditions	Yield
With sulfuric acid at 125℃; im Rohr;

3-ethoxyacrylonitrile (61310-53-0) + urea (57-13-6) → Cytosine (71-30-7)

Conditions	Yield
With sodium butanolate

di-tert-butyl dicarbonate (24424-99-5) + Cytosine (71-30-7) → C19H29N3O7 (1108637-27-9)

Conditions	Yield
With dmap In tetrahydrofuran at 70℃; for 0.116667h; Microwave irradiation; Green chemistry;	100%
With dmap In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	91%
With dmap In tetrahydrofuran

Cytosine (71-30-7) + C26H33FO6Si → C28H34FN3O5Si

Conditions	Yield
Stage #1: Cytosine With N,O-bis-(trimethylsilyl)-acetamide In 1,2-dichloro-ethane at 20℃; for 2h; Reflux; Stage #2: C26H33FO6Si With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 2h; Reflux;	100%

Cytosine (71-30-7) → 5-iodocytosine (1122-44-7)

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide for 12.5h; Sonographic reaction; Inert atmosphere;	99%
With iodine; iodic acid In acetic acid at 40℃;	96%
With iodine; iodic acid; acetic acid In tetrachloromethane; water at 50℃;	86%

N,N-dimethylformamide dipropyl acetal (6006-65-1) + Cytosine (71-30-7) → N4-<(Dimethylamino)methylene>-1-propylcytosine (79044-11-4)

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Heating;	99%

Cytosine (71-30-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N4-<(Dimethylamino)methylene>-1-methylcytosine (77738-01-3)

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Heating; other N,N-dimethylformamide dialkyl(diaralkyl) acetales;	99%
In N,N-dimethyl-formamide for 24h; Heating;	99%
trifluoroacetic acid for 15h; Heating;	98%
With trifluoroacetic acid

Cytosine (71-30-7) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → N4-<(Dimethylamino)methylene>-1-ethylcytosine (79044-10-3)

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Heating;	99%

di-tert-butyl dicarbonate (24424-99-5) + Cytosine (71-30-7) → tert-butyl 4-[bis(tert-butoxycarbonyl)amino]-2-oxopyrimidine-1(2H)-carboxylate

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; Inert atmosphere;	99%

Cytosine (71-30-7) + (propa-1,2-dien-1-yloxy)cyclohexane → (S)-4-amino-1-(1-(cyclohexyloxy)allyl)pyrimidin-2(1H)-one

Conditions	Yield
With pyridine; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane at 20℃; for 24h; Inert atmosphere; enantioselective reaction;	98.5%

Cytosine (71-30-7) + acetic anhydride (108-24-7) → 4-N-Acetylcytosine (14631-20-0)

Conditions	Yield
With phosphoric acid at 100℃; for 8h;	98%
With pyridine for 2.5h; Heating;	97.2%
With pyridine at 20℃; for 24h;	85%

N,N-dimethylformamide dipropyl acetal (6006-65-1) + Cytosine (71-30-7) → N4-<(Dimethylamino)methylene>cytosine (76299-81-5)

Conditions	Yield
With trifluoroacetic acid at 85 - 90℃; for 12h;	98%

N,N-dimethylformamide di-n-butyl acetal (18503-90-7) + Cytosine (71-30-7) → 1-Butyl-N4-<(dimethylamino)methylene>cytosine (79044-12-5)

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Heating;	98%

Cytosine (71-30-7) + 2-Methylpropionic anhydride (97-72-3) → N6-isobutyrylaminocytosine (97626-98-7)

Conditions	Yield
With pyridine for 2h; Heating;	98%
In N,N-dimethyl-formamide Heating;	80%

Cytosine (71-30-7) + dibutylformamide dineopentyl acetal → N,N-Dibutyl-N'-(2-oxo-1,2-dihydro-pyrimidin-4-yl)-formamidine

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Ambient temperature;	98%

Cytosine (71-30-7) + 2-Chloro-N-[2-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl]-acetamide (406215-03-0) → 2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-N-[2-(3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl]-acetamide (406215-10-9)

Conditions	Yield
Stage #1: Cytosine With sodium hydride; triethylamine In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 2-Chloro-N-[2-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl]-acetamide In N,N-dimethyl-formamide at 20℃; Further stages.;	98%

Cytosine (71-30-7) → 4‐amino‐[5,6‐D2]pyrimidin‐2(1H)‐one deuterium chloride

Conditions	Yield
Stage #1: Cytosine With platinum(IV) oxide; sodium tetrahydroborate; palladium on activated charcoal; water-d2 at 160℃; for 1.33333h; Microwave irradiation; Stage #2: With hydrogen chloride at 0℃;	98%

silver hexafluoroantimonate + chloromethyl(1,5-cyclooctadiene)platinum(II) + Cytosine (71-30-7) → [(1,5-cyclooctadiene)PtMe(cytosine)](SbF6) (921800-07-9, 921800-01-3, 1160938-96-4)

Conditions	Yield
In acetone (Ar); Ag salt was added to stirred soln. of Pt in acetone; stirred for 30 min; filtered; suspn. of cytosine in acetone was added; stirred for 30min; solvent removed; washed (H2O); dried (vac.); elem. anal.;	97.5%

Cytosine (71-30-7) → C4(2)H5N3O

Conditions	Yield
Stage #1: Cytosine With molybdenum(IV) oxide; sodium tetrahydroborate; palladium 10% on activated carbon; water-d2 at 20 - 160℃; for 1.83333h; Microwave irradiation; Stage #2: With hydrogen chloride In water for 0.333333h;	97.5%

Cytosine (71-30-7) → N4-sulfamoylcytosine

Conditions	Yield
With pyridine; sulfamate de pentachlorophenyle at 100℃; for 2h; regioselective transfer of the sulfamoyl group to the extracyclic NH2 group of amniopyrimidines and amonopurines;	97%
With pyridine; sulfamate de pentachlorophenyle at 100℃; for 2h;	97%

N,N-Dimethylformamide diallyl acetal (61296-25-1) + Cytosine (71-30-7) → 1-Allyl-N4-<(dimethylamino)methylene>cytosine (79044-13-6)

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Heating;	96%

Cytosine (71-30-7) + water (7732-18-5) + barium(II) perchlorate → {[Ba(cytosine)2(H2O)](ClO4)2}n

Conditions	Yield
Stage #1: Cytosine; water at 45℃; for 0.5h; Stage #2: barium(II) perchlorate at 20℃;	96%

Cytosine (71-30-7) → Flucytosine (2022-85-7)

Conditions	Yield
Stage #1: Cytosine With hydrogen fluoride at -15 - 0℃; Inert atmosphere; Stage #2: at -20℃; for 4h; Inert atmosphere; Further stages;	95.7%
With 1,1,1,3',3',3'-hexafluoro-propanol; fluorine at 20℃; under 1125.11 Torr; Temperature; Pressure; Reagent/catalyst; Inert atmosphere;	87.4%
With formic acid for 1.5h; Time; Flow reactor; Autoclave;	63%
With formic acid; fluorine at 9℃; for 0.0833333h; Temperature; Concentration; Inert atmosphere;

Cytosine (71-30-7) → 5-bromocytosine (2240-25-7)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 15℃; for 1h; Reagent/catalyst; Solvent; Sonication;	95.6%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 10h; Large scale;	93.6%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 10h;	93.6%

Cytosine (71-30-7) + 4-methoxy-benzoyl chloride (100-07-2) → N4-(4-methoxybenzoyl)-cytosine (51820-70-3)

Conditions	Yield
With pyridine at 20℃;	95%
With pyridine at 80℃; for 2h; Acylation;	93%
With pyridine at 80℃; for 2h;	81%
With pyridine; dmap In dichloromethane at 20℃; Inert atmosphere;

Cytosine (71-30-7) + tert-butyl (2R,3S,5R)-2-(acetyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]-3-(trifluoromethyl)pyrrolidine-1-carboxylate (496848-33-0) → tert-butyl (2RS,3S,5R)-2-[4-amino-2-oxopyrimidin-1(2H)-yl]-5-[(tert-butyldimethylsilyloxy)methyl]-3-(trifluoromethyl)pyrrolidine-1-carboxylate (496848-38-5)

Conditions	Yield
Stage #1: Cytosine; tert-butyl (2R,3S,5R)-2-(acetyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]-3-(trifluoromethyl)pyrrolidine-1-carboxylate With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.5h; Heating; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 16h;	95%

bis(η3-allyl-μ-chloropalladium(II)) + Cytosine (71-30-7) → η3-allylchloro(cytosine)palladium(II) (96226-53-8)

Conditions	Yield
In methanol soln. stirred for 3h, pptn (molar ratio complex : ligand = 1:2); filtered, washed (MeOH, ether), dried (vac.), elem. anal.;	95%

N-chloro-succinimide (128-09-6) + Cytosine (71-30-7) → 5-chloro-cytosine (2347-43-5)

Conditions	Yield
With acetic acid at 70 - 77℃; for 4.3h;	95%

(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-vinyltetrahydrofuran-2,3-diyl diacetate (1146197-36-5) + Cytosine (71-30-7) → (2R,3R,4S,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-5-vinyltetrahydrofuran-3-yl acetate

Conditions	Yield
Stage #1: Cytosine In acetonitrile at 20℃; for 3h; Vorbrueggen Nucleoside Synthesis; Stage #2: (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-vinyltetrahydrofuran-2,3-diyl diacetate With tin(IV) chloride In acetonitrile at 65℃; for 1h;	95%

Cytosine (71-30-7) + α-D-erythropentafuranose-2'-deoxy-2',2'-difluoro-3,5-dibenzoate-1-methanesulfonate (134877-43-3) → β-1-(2’-deoxy-2’,2’-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)-4-aminopyrimidin-2-one hydrochloride

Conditions	Yield
Stage #1: Cytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Reflux; Industrial scale; Stage #2: α-D-erythropentafuranose-2'-deoxy-2',2'-difluoro-3,5-dibenzoate-1-methanesulfonate With hydrogenchloride; phosphomolybdic acid In pentan-1-ol at 128 - 137℃; for 5h; Temperature; Solvent; Industrial scale;	95%
Stage #1: Cytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 3h; Reflux; Stage #2: α-D-erythropentafuranose-2'-deoxy-2',2'-difluoro-3,5-dibenzoate-1-methanesulfonate With phosphotungstic acid In i-Amyl alcohol at 64℃; Reagent/catalyst; Temperature; Solvent; Time; Further stages;

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + Cytosine (71-30-7) → [Ru(η6-p-cymene)(cytosine-κN4)Cl2]

Conditions	Yield
In methanol for 4h; Inert atmosphere;	95%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + Cytosine (71-30-7) → (2-oxo-1,2-dihydro-pyrimidin-4-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 2h;	95%

Upstream product

• 19981-17-0 sodium cyanamide 
• 76299-81-5 N⁴-<(Dimethylamino)methylene>cytosine 
• 2032-34-0 3,3-bis(ethyloxy)propanenitrile 
• 57-13-6 urea 
• 61310-53-0 3-ethoxyacrylonitrile 
• 32747-18-5 cytidinium sulphate 
• 61445-73-6 (4-amino-pyrimidin-2-ylsulfanyl)-acetic acid 
• 54308-63-3 2-ethylsulfanyl-pyrimidin-4-ylamine 
• 6220-43-5 4-ethoxypyrimidin-2-one 
• 3289-47-2 4-amino-2-methoxypyrimidine 
• 7461-50-9 2-chloropyrimidin-4-amine 
• 1032-65-1 cytidine 5'-(dihydrogen phosphate) 
• 5746-18-9 1-methyl-4-carboxypyridinium chloride 
• 71203-50-4 C₅₇H₇₄N₂₄O₃₇P₆ 

Downstream Products

• 99355-30-3 C₃₀H₂₅N₃O₈ 
• 4776-08-3 3-methylcytosine 
• 608-34-4 3-methyluracil 
• 1122-47-0 1-MeCyt 
• 6749-87-7 1,3-dimethylcytosine 
• 18002-27-2 1-(2-Tetrahydrofuryl)cytosin 
• 18037-10-0 2,4-O,N-bis(trimethylsilyl)cytosine 
• 2079-00-7 (+)-blasticidin S 
• 63257-29-4 N-demethylblasticidin S 
• 39007-97-1 pentopyranine C 
• 59862-05-4 cytosylglucuronic acid 
• 117011-73-1 (E)-N¹-(4-chloro-2-buten-1-yl)cytosine 
• 79044-14-7 1-Benzyl-N⁴-<(dimethylamino)methylene>cytosine 
• 85210-55-5 1,2-Bisethan-hydroiodid 

Relevant articles and documents

The aminomethylation of adenine, cytosine and guanine

-

2'-C-cyano-2'-deoxy-1-β-D-arabinofuranosyl-cytosine (CNDAC): A mechanism-based DNA-strand-breaking antitumor nucleoside

The antitumor mechanism of action of 2'-C-cyano-2'-deoxy-1-β-D- arabinofuranosyl (CNDAC) has been examined. CNDAC was designed as a potentially DNA-self-strand-breaking nucleoside. It had potent antitumor effects against various solid tumors in vitro as well as in vivo. Using a chain-extension method with Vent (exo-) DNA polymerase and a short primer/template system, we found that 5'-triphosphate of CNDAC (CNDACTP) was incorporated into the primer at a site opposite a guanine residue in the template. After further chain-extension reaction of the primer containing CNDAC at the 3'-terminus, chain elongation was not observed. Therefore, CNDACTP appeared to act as a chain-terminator. Analyses of the structure of the 3'-terminus in the primer revealed 2'-C-cyano-2',3'-didehydro-2',3'- dideoxycytidine (ddCNC) together with CNDAC and 2'-C-cyano-2'-deoxy-1-β-D- ribofuranosylcytosine (CNDC). The existence of ddCNC in the 3'-end of the primer would be due to the self-strand-break by the nucleotide incorporated next to CNDAC. We also found that CNDAC was epimerized to CNDC in near- neutral to alkaline media. Therefore, CNDC found in the primer was epimerized after incorporation of CNDACTP into the primer. We also described the metabolism of CNDAC.

Homochiral crystal generation: Via sequential dehydration and Viedma ripening

1,2-Bis(N-benzoyl-N-methylamino)benzene (2) forms centrosymmetric hydrate crystals (2·xH2O) and non-centrosymmetric anhydrous crystals. Dehydration of this hydrate (30 min at 140 °C) resulted in the formation of chiral crystals (i.e. a physical racemate of the conglomerate crystals) as verified using solid-state circular dichroism and powder X-ray diffraction. Subsequent attrition-enhanced deracemization, also known as Viedma ripening, was used to obtain homochiral crystals of 2 within 5 h.

-

-

Sources of 2,5-diaminoimidazolone lesions in DNA damage initiated by hydroxyl radical attack

The present study reports radiation-chemical yields of 2.5-diaminoimidazolone (Iz) derivatives in X-irradiated phosphate-buffered solutions of guanosine and double-stranded DNA. Various gassing conditions (air, N20/O2 (4:1), N2O, vacuum) were employed to elucidate the contribution of several alternative pathways leading to Iz in reactions initiated by hydroxyl radical attack on guanine. In all systems, Iz was identified as the second by abundance guanine degradation product after 8-oxoguanine, formed in 1:5 (guanosine) and 1:3.3 (DNA) ratio to the latter in air-saturated solutions. Experimental data strongly suggest that the addition of molecular oxygen to the neutral guanine radical G(-H)? plays a major in Iz production in oxygenated solutions of double-stranded DNA while in other systems it may compete with recombination of G(-H)? with superoxide and/or alkyl peroxyl radicals. The production of Iz through hydroxyl radical attack on 8-oxoguanine was also shown to take place although the chemical yield of Iz (ca 6%) in this process is too low to compete with the other pathways. The linearity of Iz accumulation with dose also indicates a negligible contribution of this channel to its yield in all systems.

A one-pot, water compatible synthesis of pyrimidine nucleobases under plausible prebiotic conditions

Herein, we report a new prebiotically plausible pathway towards a pyrimidine nucleobase in continuous manner. The route involves simultaneous methylation and carbamoylation of cyanoacetylene-derived α,β-unsaturated thioamide with N-methyl-N-nitrosourea (MNU) in aqueous media. This provides S-methylpyrimidinone in one-pot, which can be converted into a variety of 4-substituted pyrimidine nucleobases including cytosine and uracil.