2140-72-9

Basic information

• Product Name: 2'-O-Methylcytidine
• Synonyms: 2'-OMe-C;4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-3-methoxy-5-methylol-tetrahydrofuran-2-yl]pyrimidin-2-one;4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidin-2-one;4-azanyl-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-oxolan-2-yl]pyrimidin-2-one;2'-OMe Cytidine;4-aMino-1-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)-3-Methoxyoxolan-2-yl]-1,2-dihydropyriMidin-2-one;2'-O-Methylcytidine, >=99%;2'-O-METHYLCYTIDINE
• CAS NO: 2140-72-9
• Molecular Formula: C₁₀H₁₅N₃O₅
• Molecular Weight: 257.24
• EINECS: 2017-001-1
• Product Categories: Nucleosides, Nucleotides, Oligonucleotides;Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Nucleotides;Biochemicals and Reagents;Nucleoside Analogs
• Mol File: 2140-72-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 252-253 C
• Boiling Point: 506 °C at 760 mmHg
• Flash Point: 259.8 °C
• Appearance: White to Off-white/Powder
• Density: 1.68 g/cm³
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO.
• PKA: 13.37±0.70(Predicted)
• CAS DataBase Reference: 2'-O-Methylcytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-O-Methylcytidine(2140-72-9)
• EPA Substance Registry System: 2'-O-Methylcytidine(2140-72-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2140-72-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 2140-72-9 differently. You can refer to the following data:
1. 2'-O-Methylcytidine is used in the preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.
2. Cytidine analog.

Synthetic route

3',5'-di-O-acetyl-2'-O-methylcytidine (1085342-86-4) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With ammonia In methanol at 20℃;	99%

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine (97626-19-2) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	96%

N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine (73793-16-5) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With ammonia In methanol at 4℃; for 48h;	80%

magnesium ethylate (2414-98-4) + 2,2'-anhydrocytidine hydrochloride → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In methanol for 5h; Reflux;	76%

diazomethane (186581-53-3, 908094-01-9) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With tin(ll) chloride In methanol; 1,2-dimethoxyethane for 0.333333h; Ambient temperature;	A 14% B 69%
dibutyldimethoxytin In methanol Mechanism;
dibutyldimethoxytin In methanol

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9) + N3-methylcytidine (2140-64-9)

Conditions	Yield
With copper acetylacetonate In N,N-dimethyl-formamide at 70℃; for 1h;	A 22% B 60% C 3%
In N,N-dimethyl-formamide at 70℃; for 1h;	A 7% B 28% C 13%
With copper acetylacetonate In N,N-dimethyl-formamide at 70℃; for 1h; Product distribution; without metallo-organic compound;
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Title compound not separated from byproducts;	A 7 % Spectr. B 28 % Spectr. C 13 % Spectr.
In methanol; N,N-dimethyl-formamide at 70℃; Title compound not separated from byproducts;	A n/a B 28 % Spectr. C 13 % Spectr.

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With magnesium(II) acetylacetonate In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Product distribution; absence of metal ion;	A 2% B 43%
With magnesium(II) acetylacetonate In methanol; N,N-dimethyl-formamide at 70℃; for 1h;	A 2% B 43%

trimethylphenylammonium hydroxide (1899-02-1) + CYTIDINE (65-46-3) → 3-methyluridine (2140-69-4) + 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃;	A n/a B 3 % Spectr. C 24%
In N,N-dimethyl-formamide at 100℃;	A 22 % Spectr. B 4 % Spectr. C 21%

1-methyl-1-nitrosourea (684-93-5) + CYTIDINE (65-46-3) → 2'-O-methylcytidine (2140-72-9) + N3-methylcytidine (2140-64-9)

Conditions	Yield
With borax In water; formamide at 50℃; for 18h;	A 5% B n/a

CYTIDINE (65-46-3) + methyl iodide (74-88-4) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With sodium hydride 1) DMF, 0 deg C, 45 min, 2a) 0 deg C, 2.5 h, 2b) r.t., 1 h; Multistep reaction. Yields of byproduct given;
With sodium hydride 1) DMF, 0 deg C, 45 min, 2a) 0 deg C, 2.5 h, 2b) r.t., 1 h; Yield given. Multistep reaction;

N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-3-methyl-butyramide → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With dichloro-acetic acid; ammonium hydroxide

Trimethyl borate (121-43-7) + 2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate (10212-28-9) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With methanol; boron trifluoride for 48h; Ring cleavage; Heating;

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-4-(2-nitrophenyl)-2-pyrimidinone (108782-90-7) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / silver oxide / acetone / 72 h / 20 °C 2: 75 percent / ammonia / tetrahydrofuran 3: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-2'-O-methyl-4-(2-nitrophenyl)-2-pyrimidinone (110567-19-6) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / ammonia / tetrahydrofuran 2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

4-(2-Nitro-phenoxy)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 2: 81 percent / silver oxide / acetone / 72 h / 20 °C 3: 75 percent / ammonia / tetrahydrofuran 4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine (415903-48-9) → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 2: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 3: 81 percent / silver oxide / acetone / 72 h / 20 °C 4: 75 percent / ammonia / tetrahydrofuran 5: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

uridine (58-96-8) + aqueous H3PO4 → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: pyridine / 20 °C 2: triethylamine / CH2Cl2 / 0.25 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 4: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 5: 81 percent / silver oxide / acetone / 72 h / 20 °C 6: 75 percent / ammonia / tetrahydrofuran 7: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: triethylamine / CH2Cl2 / 0.25 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 3: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 4: 81 percent / silver oxide / acetone / 72 h / 20 °C 5: 75 percent / ammonia / tetrahydrofuran 6: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose (68045-07-8) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) HMDS, (NH4)2SO4, 2.) SnCl4 / 1.) reflux, overnight, 2.) dichloroethane, reflux, 60 min 2: 80 percent / NH3 / methanol / 48 h / 4 °C View Scheme

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / BF3*(C2H5)2O / CH2Cl2 / 0 °C 2: 1.) HMDS, (NH4)2SO4, 2.) SnCl4 / 1.) reflux, overnight, 2.) dichloroethane, reflux, 60 min 3: 80 percent / NH3 / methanol / 48 h / 4 °C View Scheme

methanol-dichloromethane + CYTIDINE (65-46-3) + methyl iodide (74-88-4) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In N-methyl-acetamide; methanol; ethanol; dichloromethane

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-methylcytidine (2140-72-9) → 5'-O-(tert-butyldimethylsilyl)-2'-O-methylcytidine (1171006-87-3)

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine at 20℃;	100%
With pyridine at 20℃;

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + 2'-O-methylcytidine (2140-72-9) → 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine (97626-19-2)

Conditions	Yield
With pyridine for 1h; Ambient temperature;	98%

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-methylcytidine (2140-72-9) → 3',5'-O-bis(tert-butyldimethylsilyl)-2'-O-methylcytidine (367511-42-0)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;	97.5%

2'-O-methylcytidine (2140-72-9) → 5-bromo-2'-O-methylcytidine (494210-77-4)

Conditions	Yield
With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 1.5h;	78%

trimethylsulphonium iodide (2181-42-2) + 2'-O-methylcytidine (2140-72-9) → 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one (120057-51-4)

Conditions	Yield
In N,N-dimethyl-formamide at 85℃; for 3.5h; Rate constant; Product distribution; Mechanism; other nucleosides and trimethylsulphonium hydroxide;	67%
In N,N-dimethyl-formamide at 85℃; for 3.5h;	67%

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester (1337529-56-2) + 2'-O-methylcytidine (2140-72-9) → C22H31N4O9P

Conditions	Yield
Stage #1: 2'-O-methylcytidine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: (S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere;	16.3%

benzoic acid anhydride (93-97-0) + 2'-O-methylcytidine (2140-72-9) → 2'-O-methyl-N4-benzoylcytidine (52571-45-6)

Conditions	Yield
In ethanol for 1h; Heating;	0.38 g

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 2'-O-methylcytidine (2140-72-9) → 2'-O-methyl-4-N-(9-fluorenylmethoxycarbonyl)cytidine (135944-10-4)

Conditions	Yield
Yield given. Multistep reaction;

trimethylsulphonium hydroxide (17287-03-5) + 2'-O-methylcytidine (2140-72-9) → 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one (120057-51-4) + N4,O2'-dimethylcytidine (13048-95-8) + O2',O3'-dimethyl-cytidine (34218-86-5)

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Title compound not separated from byproducts;	A 34 % Spectr. B 21 % Spectr. C 8 % Spectr.

2'-O-methylcytidine (2140-72-9) → 5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine (86872-24-4)

Conditions	Yield
Multistep reaction;

chloro-trimethyl-silane (75-77-4) + 2'-O-methylcytidine (2140-72-9) → 4-Amino-1-((2R,3R,4R,5R)-3-methoxy-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

Conditions	Yield
In pyridine 0 deg C -> r.t. for 1-2 h;
With pyridine Silylation;

acetic anhydride (108-24-7) + 2'-O-methylcytidine (2140-72-9) → N4-acetyl-2'-O-methyl cytidine (113886-71-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Acetylation;	0.94 g

2'-O-methylcytidine (2140-72-9) → 5-bromo-3'-O-[(tert-butyldimethyl)silyl]-2'-O-methylcytidine (444019-26-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: 83 percent / LiBr; ammonium ceric(IV) nitrate / acetonitrile / 3 h / 20 °C 3: 40 percent / aq. AcOH / 6 h / 50 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 5-bromo-3',5'-O-bis[(tert-butyldimethyl)silyl]-2'-O-methylcytidine (848860-93-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: 83 percent / LiBr; ammonium ceric(IV) nitrate / acetonitrile / 3 h / 20 °C View Scheme

2'-O-methylcytidine (2140-72-9) → N4-(4,4'-dimethoxytrityl)-2'-O-methylcytidine (444019-24-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: DMAP; pyridine / 20 °C 3: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 2,2-dimethyl-thiopropionic acid S-(2-{[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-yloxy]-[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-phosphoryloxy}-ethyl) ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2.1: DMAP; pyridine / 20 °C 3.1: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C 4.1: 1H-tetrazole / acetonitrile / 20 °C 4.2: 3-chloroperbenzoic acid / CH2Cl2 / 20 °C 4.3: aq. AcOH / methanol / 55 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 2'-O-methylcytidine-5'-[bis-(S-pivaloyl-2-thioethyl)phosphate]

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2.1: DMAP; pyridine / 20 °C 3.1: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C 4.1: 1H-tetrazole / acetonitrile / 20 °C 4.2: 3-chloroperbenzoic acid / CH2Cl2 / 20 °C 4.3: 22 percent / aq. AcOH / methanol / 55 °C View Scheme

Upstream product

• 186581-53-3 diazomethane 
• 65-46-3 CYTIDINE 
• 17287-03-5 trimethylsulphonium hydroxide 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 74-88-4 methyl iodide 
• 121-43-7 Trimethyl borate 
• 10212-28-9 2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate 
• 684-93-5 1-methyl-1-nitrosourea 
• 2414-98-4 magnesium ethylate 
• 1085342-86-4 3',5'-di-O-acetyl-2'-O-methylcytidine 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 68045-07-8 1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose 
• 69304-38-7 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 58-96-8 uridine 

Downstream Products

• 52571-45-6 2'-O-methyl-N⁴-benzoylcytidine 
• 444019-24-3 N⁴-(4,4'-dimethoxytrityl)-2'-O-methylcytidine 
• 113886-71-8 N⁴-acetyl-2'-O-methyl cytidine 
• 86872-24-4 5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine 
• 120057-51-4 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one 
• 13048-95-8 N4,2'-O-dimethylcytidine 
• 34218-86-5 O^2'_,O3'-dimethyl-cytidine 
• 110764-74-4 N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-methylcytidine 

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