[ CAS No. 1147-23-5 ] {[proInfo.proName]}

Name: 1147-23-5|5-Iodo-cytidine|98%
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2D 3D

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Quality Control of [ 1147-23-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1147-23-5 ]

SDS Specification

Alternatived Products of [ 1147-23-5 ]

Product Details of [ 1147-23-5 ]

CAS No. :	1147-23-5	MDL No. :	MFCD00056070
Formula :	C₉H₁₂IN₃O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LQQGJDJXUSAEMZ-UAKXSSHOSA-N
M.W :	369.11	Pubchem ID :	159359
Synonyms :	5-Iodo-D-cytidine

Calculated chemistry of [ 1147-23-5 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	4.0
Molar Refractivity :	68.56
TPSA :	130.83 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-9.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.25
Log Po/w (XLOGP3) :	-1.72
Log Po/w (WLOGP) :	-2.27
Log Po/w (MLOGP) :	-1.02
Log Po/w (SILICOS-IT) :	-1.27
Consensus Log Po/w :	-1.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.16
Solubility :	25.6 mg/ml ; 0.0693 mol/l
Class :	Very soluble
Log S (Ali) :	-0.51
Solubility :	113.0 mg/ml ; 0.306 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.12
Solubility :	487.0 mg/ml ; 1.32 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.06

Safety of [ 1147-23-5 ]

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 [ 1147-23-5 ]

* 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 [ 1147-23-5 ]
Downstream synthetic route of [ 1147-23-5 ]

[ 1147-23-5 ] Synthesis Path-Upstream 1~1

1
[ 65-46-3 ]
[ 1147-23-5 ]

Yield	Reaction Conditions	Operation in experiment
85.1%	With iodine; iodic acid; acetic acid In tetrachloromethane; water at 20 - 40℃;	Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachioride was warmed to 40 CC, and iodine (9.6 g, 75.7 mmol) was added.To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 mm. The reaction mixture was stirred at 40 CC for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane—methanol(15:1 to 10:1 to5:1) asgradienteluents resulting in 19.4g (85.1percent) desiredproduct 5-iodocytidine (191).
85.1%	With iodine; iodic acid In tetrachloromethane; water; acetic acid at 40℃; for 6 h;	Synthesis of 5-iodocytidine 1 91 : A mixture of cytidine 190 (15.0 g, 61 .7 mmol) in 225 mL of acetic d and 225 mL of carbon tetrachloride was warmed to 40 °C, and iodine (9.6 g, 75.7 mmol) was added. the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of ter within 10 min. The reaction mixture was stirred at 40 °C for 6 h and stirred at room temperature ernight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated der reduced pressure. The residue was purified by flash chromatography on a silica gel column using hloromethane-methanol (15:1 to 1 0:1 to 5:1 ) as gradient eluents resulting in 1 9.4 g (85.1 percent) desired duct 5-iodocytidine (191 ).
85.1%	With iodine; iodic acid; acetic acid In tetrachloromethane; water at 20 - 40℃;	Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachloride was warmed to 40 °C, and iodine (9.6 g, 75.7 mmol) was added. To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 min. The reaction mixture was stirred at 40 °C for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane-methanol (15:1 to 10:1 to 5:1) as gradient eluents resulting in 19.4 g (85.1 percent) desired product 5-iodocytidine (191).

72.4%	With N-iodo-succinimide In methanol at 40 - 70℃;	The cytidine (0.66 g, 2.7 mol) was added to the three-necked flask,N-iodosuccinimide (0.60 g, 2.4 mol) and 50 ml of methanol, and the temperature was raised to 40-70 ° C. The reaction was stirred for 6-12 hours.Cooled to room temperature, filtered, added with silica gel and removed by rotary evaporation. The column chromatography gave 0.48 g of a pale yellow solid in 72.4percent yield.
51%	With iodine; iodic acid; acetic acid In tetrachloromethane; water at 40℃; for 2 h;	General procedure: The suspension of nucleosides 2a,b (19 mmol) in water (5.7 mL) was treated with HIO3(9.7 mmol, 1.7 g), AcOH (15.2 mL) and a solution of iodine (11.22 mmol, 2.85 g) inCCl4 (3.8 mL). The resulting mixture was stirred at 40C for 2 h until the starting materialwas consumed or some by-product was formed (monitored by HPLC). After that,water (20 mL) was added. The reaction mixture was cooled to 4C and filtered. The precipitatewas washed with water (2 £ 10 mL). The combined solutions were diluted withwater (250 ml) and extracted with benzene (3 £ 150 mL). The aqueous layer was evaporatedunder reduced pressure. The product was purified by RPC in a linear gradient ofEtOH in water (0–30percent) to give the product 3a,b.

Reference： [1] Patent: WO2015/196130, 2015, A2, . Location in patent: Page/Page column 634; 635
[2] Patent: WO2015/196128, 2015, A2, . Location in patent: Page/Page column 642
[3] Patent: EP2918275, 2015, A1, . Location in patent: Paragraph 2219; 2220
[4] Patent: EP2918275, 2016, B1, . Location in patent: Paragraph 2219; 2220
[5] Journal of the American Chemical Society, 2015, vol. 137, # 1, p. 34 - 37
[6] Synthesis, 2003, # 7, p. 1039 - 1042
[7] Patent: CN106674316, 2017, A, . Location in patent: Paragraph 0015-0016; 0019-0020
[8] Synthesis, 2009, # 23, p. 3957 - 3962
[9] Tetrahedron Letters, 1999, vol. 40, # 51, p. 8961 - 8964
[10] Organic Preparations and Procedures International, 2018, vol. 50, # 3, p. 332 - 342
[11] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 8, p. 2688 - 2697

[ 1147-23-5 ] Synthesis Path-Downstream 1~74

1
[ 1147-23-5 ]
[ 42386-74-3 ]

Reference： [1]Journal of Organic Chemistry,1974,vol. 39,p. 2182 - 2186

2
[ 107-13-1 ]
[ 1147-23-5 ]
[ 138638-28-5 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 627 - 630

3
[ 292638-85-8 ]
[ 1147-23-5 ]
[ 81244-97-5 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 627 - 630

4
[ 1147-23-5 ]
[ 23276-37-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 2688 - 2697

5
[ 65-46-3 ]
[ 1147-23-5 ]

Yield	Reaction Conditions	Operation in experiment
85.1%	With iodine; iodic acid; acetic acid; In tetrachloromethane; water; at 20 - 40℃;	Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachioride was warmed to 40 CC, and iodine (9.6 g, 75.7 mmol) was added.To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 mm. The reaction mixture was stirred at 40 CC for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane-methanol(15:1 to 10:1 to5:1) asgradienteluents resulting in 19.4g (85.1%) desiredproduct 5-iodocytidine (191).
85.1%	With iodine; iodic acid; In tetrachloromethane; water; acetic acid; at 40℃; for 6h;	Synthesis of 5-iodocytidine 1 91 : A mixture of cytidine 190 (15.0 g, 61 .7 mmol) in 225 mL of acetic d and 225 mL of carbon tetrachloride was warmed to 40 C, and iodine (9.6 g, 75.7 mmol) was added. the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of ter within 10 min. The reaction mixture was stirred at 40 C for 6 h and stirred at room temperature ernight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated der reduced pressure. The residue was purified by flash chromatography on a silica gel column using hloromethane-methanol (15:1 to 1 0:1 to 5:1 ) as gradient eluents resulting in 1 9.4 g (85.1 %) desired duct 5-iodocytidine (191 ).
85.1%	With iodine; iodic acid; acetic acid; In tetrachloromethane; water; at 20 - 40℃;	Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachloride was warmed to 40 C, and iodine (9.6 g, 75.7 mmol) was added. To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 min. The reaction mixture was stirred at 40 C for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane-methanol (15:1 to 10:1 to 5:1) as gradient eluents resulting in 19.4 g (85.1 %) desired product 5-iodocytidine (191).

72.4%	With N-iodo-succinimide; In methanol; at 40 - 70℃;	The cytidine (0.66 g, 2.7 mol) was added to the three-necked flask,N-iodosuccinimide (0.60 g, 2.4 mol) and 50 ml of methanol, and the temperature was raised to 40-70 C. The reaction was stirred for 6-12 hours.Cooled to room temperature, filtered, added with silica gel and removed by rotary evaporation. The column chromatography gave 0.48 g of a pale yellow solid in 72.4% yield.
51%	With iodine; iodic acid; acetic acid; In tetrachloromethane; water; at 40℃; for 2h;	General procedure: The suspension of nucleosides 2a,b (19 mmol) in water (5.7 mL) was treated with HIO3(9.7 mmol, 1.7 g), AcOH (15.2 mL) and a solution of iodine (11.22 mmol, 2.85 g) inCCl4 (3.8 mL). The resulting mixture was stirred at 40C for 2 h until the starting materialwas consumed or some by-product was formed (monitored by HPLC). After that,water (20 mL) was added. The reaction mixture was cooled to 4C and filtered. The precipitatewas washed with water (2 £ 10 mL). The combined solutions were diluted withwater (250 ml) and extracted with benzene (3 £ 150 mL). The aqueous layer was evaporatedunder reduced pressure. The product was purified by RPC in a linear gradient ofEtOH in water (0-30%) to give the product 3a,b.

Reference： [1]Patent: WO2015/196130,2015,A2 .Location in patent: Page/Page column 634; 635
[2]Patent: WO2015/196128,2015,A2 .Location in patent: Page/Page column 642
[3]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2219; 2220
[4]Journal of the American Chemical Society,2015,vol. 137,p. 34 - 37
[5]Synthesis,2003,p. 1039 - 1042
[6]Patent: CN106674316,2017,A .Location in patent: Paragraph 0015-0016; 0019-0020
[7]Synthesis,2009,p. 3957 - 3962
[8]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964
[9]Organic Preparations and Procedures International,2018,vol. 50,p. 332 - 342
[10]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 2688 - 2697

6
[ 75-77-4 ]
[ 1147-23-5 ]
4-Amino-1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-1H-pyrimidin-2-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964

9
[ 1147-23-5 ]
[ 256493-88-6 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964

10
[ 1147-23-5 ]
N-[1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964

11
[ 1147-23-5 ]
[ 256493-89-7 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964

12
[ 1147-23-5 ]
N-{1-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-5-iodo-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964

13
[ 1147-23-5 ]
[ 256493-90-0 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964
[2]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964

14
[ 1147-23-5 ]
diisopropyl-phosphoramidous acid 5-(4-benzoylamino-5-iodo-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964
[2]Tetrahedron Letters,1999,vol. 40,p. 8961 - 8964

15
[ 1147-23-5 ]
[ 81206-84-0 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 627 - 630

16
[ 1147-23-5 ]
[ 137248-66-9 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 627 - 630

17
[ 1147-23-5 ]
(2S)-2-(butyryloxymethyl)-5-acetoxy-2,3,4,5-tetrahydro-3-thiafuran [ No CAS ]
[ 181624-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tin(IV) chloride;	Coupling of 1-O-acetyl-5'-butyryl-3-thiafuranose with 5 -iodo-cytidine using tin chloride afforded the protected b-isomer of 5'-butyryl-2',3'-deoxy-5-iodo-3'-thia-cytidine with good stereoselectivity. To a solution of 5'-butyryl-2',3'-deoxy-5-iodo-3'-thiacytidine (1.63 g; 3.83 mmol) in 100 ml of anhydrous MeOH was added tetrakis-(triphenylphosphine)palladium (0) (0.16 g, 0.14 mmol) and Et3N (0.8 ml). The reaction mixture was maintained under a CO atmosphere for 6 h while heating at 40 C. The solution was concentrated to dryness in vacuo, dissolved in CH2Cl1 then filtered. The resultant precipitate was dissolved in hot CHCl3 to give after crystallization the desired product 5-carboxylic acid methyl ester-2',3'-dideoxy-3'-thiacytidine (0.7 g, 62%) as a white solid. m.p. 217-221C.; 1H NMR (DMSO) d 3.2-3.3 (m, 2H, H-2' and H-2), 3.75 (s, 3H, OCH3), 3.8-4.0 (m, 2H H-5' and H-5), 5.36 (m, 1H, OH-5'), 5.49 (t, 1H, H-4', J4',5'=4.0, 6.21 (m, 1H, H-1'), 7.7 and 8.1 (2 br s, 1H each, NH2), 9.0 (s, 1H, H-6); m/z (LSIMS) 288 (M+H)+; Anal. (C10H13N3O5S) C, H, N, S. To a solution of 5-carboxylic acid methyl ester-2',3' -dideoxy-3'-thiacytidine (0.2 g, 0.69 mmol) in anhydrous MeOH was added (50 ml) a 2 M solution at of NH3-MeOH and a catalytic amount of NaCN (20 mg). The resulting solution was stirred at 100 degrees for 20 h and then concentrated in vacuo. The residue was chromatographed on silica gel using CH2Cl2/MeOH (90:10) as eluent to give 5-carboxylic acid amide-2',3'-dideoxy-3'-thiacytidine (0.12 g, 63%) as a white solid. m.p. 190-192 degrees; 1H NMR (DMSO) d 3.18 (dd, 1H, H-2' or H-2, J2',2=10.2, J2'or 2,1'=1.4), 3.41 (dd, 1H, H-2' or H-2, J2',2=10.1, J2'or 2,1'=1.5), 3.8-4.0 (m, 2H , H-5' and H-5), 5.36 (t, 1H, H-4', J4',5'=4.0), 5.5 (br s, 1H, OH-5'), 6.21 (dd, 1H, H-1', J1',2'or 2=4.3, J1',2'or 2=1.9), 7.5 (br s, 2H, NH2), 7.8 and 8.4 (2 br s, 1H each, NH2), 8.6 (s, 1H, H-6); m/z (LSIMS) 273 (M+H)+; Anal. (C9H12N4O4S) C, H, N, S.

Reference： [1]Patent: US6391859,2002,B1 .Location in patent: Page column 11

18
[ 14719-21-2 ]
[ 1147-23-5 ]
[ 480439-97-2 ]

Yield	Reaction Conditions	Operation in experiment
67%	With copper(l) iodide; triethylamine;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 19 - 22℃;Inert atmosphere;	A 100-mL three-necked flask was charged with <strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong> (2.66 g, 7.00 mmol, 1.00 equiv.), cuprous iodide (0.267 g, 1.40 mmol, 0.20 equiv.) and dry DMF (35 mL). After complete dissolution of the reaction mixture, propargyltrifluoroacetamide (3.17 g, 21.00 mmol, 3.00 equiv.), triethylamine (1.42 g, 14.00 mmol, 2.00 equiv.) and finally tetrakis (triphenylphosphine)palladium(0) (0.809 g, 0.70 mmol, 0.10 equiv.) were added to the reaction mixture under N2. The reaction was stirred at ambient temperature (around 19 C. to around 22 C.) under N2 for 18-24 h. The reaction was then diluted with 70 mL of 1:1 methanol-dichloromethane and the bicarbonate form of AGI X8 resin (12.00 g) was added. After stirring for about one h, the reaction mixture was filtered and the resin was washed with 1:1 methanol-dichloromethane. The combined filtrates were rapidly concentrated with a rotary evaporator. The residue was immediately purified by flash chromatography. Removal of solvent from the appropriate fractions afforded 1.84 g (67%) of 5-[3-(trifluoroacetamido)propynyl]cytidine as a light brown solid, which was confirmed by 1H-NMR.
67%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 19 - 22℃;Inert atmosphere;	A 100-mL three-necked flask was charged with <strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong> (2.66 g, 7.00 mmol, 1.00 equiv.), cuprous iodide (0.267 g, 1.40 mmol, 0.20 equiv.) and dry DMF (35 mL). After complete dissolution of the reaction mixture, propargyltrifluoroacetamide (3.17 g, 21.00 mmol, 3.00 equiv.), triethylamine (1.42 g, 14.00 mmol, 2.00 equiv.) and finally tetrakis (triphenylphosphine)palladium(0) (0.809 g, 0.70 mmol, 0.10 equiv.) were added to the reaction mixture under N2. The reaction was stirred at ambient temperature (around 19C to around 22C) under N2 for 18-24 h. The reaction was then diluted with 70 mL of 1:1 methanol-dichloromethane and the bicarbonate form of AGI X8 resin (12.00 g) was added. After stirring for about one h, the reaction mixture was filtered and the resin was washed with 1:1 methanol-dichloromethane. The combined filtrates were rapidly concentrated with a rotary evaporator. The residue was immediately purified by flash chromatography. Removal of solvent from the appropriate fractions afforded 1.84 g (67 %) of 5-[3-(trifluoroacetamido)propynyl]cytidine as a light brown solid, which was confirmed by 1H-NMR.

Reference： [1]Chemical Communications,2014,vol. 50,p. 7844 - 7847
[2]Patent: US2012/252691,2012,A1 .Location in patent: Page/Page column 34
[3]Patent: EP2669291,2013,A1 .Location in patent: Paragraph 0029; 0109

19
[ 1147-23-5 ]
[ 1340586-68-6 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 7844 - 7847

20
[ 1147-23-5 ]
5-[3-((E)-cyclooct-4-enyloxyacetamido)propyl]cytidine [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 7844 - 7847

21
[ 1147-23-5 ]
5-[3-((E)-cyclooct-4-enyloxyacetamido)propyl]cytidine-5'-triphosphate [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 7844 - 7847

22
[ 14719-21-2 ]
[ 1147-23-5 ]
[ 1340586-67-5 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 7844 - 7847

23
[ 1147-23-5 ]
C₃₃H₄₁N₁₁O₁₁ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 34 - 37

24
[ 1147-23-5 ]
5-azidopentynyl cytidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 34 - 37

25
[ 14267-92-6 ]
[ 1147-23-5 ]
5-chloropentyn-1-yl cytidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 34 - 37

26
[ 75-09-2 ]
[ 1147-23-5 ]
[ 98-80-6 ]
[ 83866-19-7 ]

Yield	Reaction Conditions	Operation in experiment
8.1%	With potassium carbonate; In methanol; water; acetonitrile;	To a stirred solution of <strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong> (200) (10.0 g, 27 mmol) in 100 mL of water and 50 mL acetonitrile was added Pd(Ac)2 (0.58 g, 2.6 mmol), followed by the addition of phenyl boronic acid (4.68 g, 38.4 mmol) and potassium carbonate (7.0 g, 50.4 mmol). The resulted reaction mixture was stirred at 80 C overnight and concentrated under reduced pressure to half volume. The precipitated solid was filtered off, and the filtrate was further concentrated. The residue was triturated with methanol, and filtered. The filtrate was concentrated partially, and the resulted solution was directly purified by flash chromatography on a silica gel column using dichloromethane - methanol (8:1 to 5:1) as gradient eluents giving 710 mg (8.1 %) product, which was further treated with methanol giving product 201 with 96% purity. 1HNMR (400 MHz, DMSO-d6); delta 8.06 (s, 1 H), 7.66 (bs, 1 H), 7.32-7.48 (m, 5H), 6.72 (bs, 1 H), 5.81 (d, 1 H, J = 3.6 Hz), 5.37 (m, 1 H), 5.67 (m, 1 H), 4.99 (m, 1 H), 3.97-4.02 (m, 3H), 3.83-3.86 (m, 1 H), 3.50-3.68 (m, 2H); MS (ESI) m/z 320 (M + H)+, 639 (2M + H)+, 660 (2M + Na)+. UV, lambdamax at 202, 232 and 282 nm.

Reference： [1]Patent: EP2918275,2015,A1

27
[ 1147-23-5 ]
[ 59259-76-6 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 16613 - 16619

28
[ 1147-23-5 ]
(x)C₆H₁₅N*C₁₃H₂₁N₆O₁₄P₃ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 16613 - 16619

29
[ 1147-23-5 ]
[ 65223-78-1 ]

Reference： [1]Patent: WO2015/196130,2015,A2
[2]Patent: WO2015/196128,2015,A2
[3]Organic and Biomolecular Chemistry,2018,vol. 16,p. 5800 - 5807
[4]Patent: EP2918275,2015,A1
[5]Tetrahedron Letters,2018,vol. 59,p. 3912 - 3915

30
[ 1147-23-5 ]
C₃₉H₃₁N₃O₉ [ No CAS ]

Reference： [1]Patent: WO2015/196130,2015,A2
[2]Patent: EP2918275,2015,A1

31
[ 1147-23-5 ]
5-ethynylcytidine-TP tetrakistriethylammonium salt [ No CAS ]

Reference： [1]Patent: WO2015/196130,2015,A2

32
[ 1147-23-5 ]
5-phenyl-CTP tetrakistriethylammonium salt [ No CAS ]

Reference： [1]Patent: WO2015/196130,2015,A2

33
[ 98-88-4 ]
[ 1147-23-5 ]
C₃₇H₂₈IN₃O₉ [ No CAS ]

Reference： [1]Patent: WO2015/196130,2015,A2 .Location in patent: Page/Page column 635
[2]Patent: WO2015/196128,2015,A2 .Location in patent: Page/Page column 642; 643
[3]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2219

34
[ 1147-23-5 ]
[ 1066-54-2 ]
4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 35℃; for 4.5h;Inert atmosphere;	Synthesis of compound 192: 5-lodocytidine (191) (2.3 g, 6.2 mmol) was dissolved in anhydrous N,N-dimethylformamide (1 00 mL), and dried triethylamine (80 mL) was added. To the nitrogen-protected stirred reaction mixture were added Cul (0.8 g, 4.2 mmol), Pd(PPh3)4 (1 .0 g, 0.87 mmol), andtrimethylsilylacetylene (1.1 g, 11.2 mmol). The resulted reaction mixture was stirred at 35 CC for 4.5 h until the starting material was consumed as monitored by TLC. The volatiles were evaporated under reduced pressure, and the residue was treated with methanol. It was filtered through a pad of Celite, and the filtrate was concentrated. The residue was purified by flash chromatography on a silica gel column using dichloromethane-methanol (10:1 to 5:1 to 3:1) as gradient eluents giving 2.0 g (94%) compound192.
94%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 35℃; for 4.5h;Inert atmosphere;	Synthesis of compound 1 92: 5-lodocytidine (191 ) (2.3 g, 6.2 mmol) was dissolved in anhydrous V-dimethylformamide (1 00 mL), and dried triethylamine (80 mL) was added. To the nitrogen-protected red reaction mixture were added Cul (0.8 g, 4.2 mmol), Pd(PPh3)4 (1 .0 g, 0.87 mmol), and methylsilylacetylene (1 .1 g, 1 1 .2 mmol). The resulted reaction mixture was stirred at 35 C for 4.5 h il the starting material was consumed as monitored by TLC. The volatiles were evaporated under uced pressure, and the residue was treated with methanol. It was filtered through a pad of Celite, and filtrate was concentrated. The residue was purified by flash chromatography on a silica gel column ng dichloromethane-methanol (1 0:1 to 5:1 to 3:1 ) as gradient eluents giving 2.0 g (94%) compound 2.
94%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 35℃; for 4.5h;Inert atmosphere;	Synthesis of compound 192: 5-lodocytidine (191) (2.3 g, 6.2 mmol) was dissolved in anhydrous N,N-dimethylformamide (100 mL), and dried triethylamine (80 mL) was added. To the nitrogen-protected stirred reaction mixture were added Cul (0.8 g, 4.2 mmol), Pd(PPh3)4 (1.0 g, 0.87 mmol), and trimethylsilylacetylene (1.1 g, 11.2 mmol). The resulted reaction mixture was stirred at 35 C for 4.5 h until the starting material was consumed as monitored by TLC. The volatiles were evaporated under reduced pressure, and the residue was treated with methanol. It was filtered through a pad of Celite, and the filtrate was concentrated. The residue was purified by flash chromatography on a silica gel column using dichloromethane-methanol (10:1 to 5:1 to 3:1) as gradient eluents giving 2.0 g (94%) compound 192.

80%

With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 35℃;

[1147-23-5]5-[1147-23-5]iodocytidine (2.71 mmol, 1 eq), CuI (1.84 mmol, 0.68 eq), and Pd(PPh3)4 (0.379 mmol, 0.14 eq) were dissolved in dry DMF (45 mL) and dry TEA (35 mL). Then TMSA (4.90 mmol, 0.698 mL, 1.81 eq) was added and the reaction was heated to 35 C and left to stir overnight. Volatiles were evaporated and the residue was treated with methanol and filtered over a pad of Celite. The filtrate was concentrated and the residue was purified by silica FC (0 to 10 % MeOH/DCM) to yield 0.733 g (80 % yield) of product 1 as a tan solid. 1H NMR (500 MHz, DMSO) delta 8.34 (s, 1H), 7.80 (s, 1H), 6.64 (s, 1H), 5.78 (d, J=3.4 Hz, 1H), 5.37 (d, J=4.8 Hz, 1H), 5.18 (t, J=5 Hz, 1H), 5.00 (d, J=5.2 Hz, 1H), 3.99-3.96 (m, 2H), 3.87-3.85 (m, 1H), 3.75-3.71 (m, 1H), 3.61-3.57 (m, 1H), 0.24 (s, 9H). 13C NMR (500 MHz, DMSO) delta 164.36, 153.97, 146.26, 100.03, 97.37, 89.84, 84.53, 74.67, 69.29, 60.42, 0.40. HRMS: Theoretical 362.1148 [M+Na+], Observed 362.1152 [M+Na+].

Reference： [1]Patent: WO2015/196130,2015,A2 .Location in patent: Page/Page column 634
[2]Patent: WO2015/196128,2015,A2 .Location in patent: Page/Page column 642
[3]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2215; 2217
[4]Organic and Biomolecular Chemistry,2018,vol. 16,p. 5800 - 5807
[5]Tetrahedron Letters,2018,vol. 59,p. 3912 - 3915

35
[ 1147-23-5 ]
[ 98-80-6 ]
[ 83866-19-7 ]

Yield	Reaction Conditions	Operation in experiment
8.1%	With palladium diacetate; potassium carbonate; In water; acetonitrile; at 80℃;	Synthesis of 5-phenyl cytidine 201: To a stirred solution of <strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong> (200) (10.0 g, 27 mmol) in 100 mL of water and 50 mL acetonitrile was added Pd(Ac)2 (0.58 g, 2.6 mmol), followed by the addition of phenyl boronic acid (4.68 g, 38.4 mmol) and potassium carbonate (7.0 g, 50.4 mmol). The resulted reaction mixture was stirred at 80 00 overnight and concentrated under reducedpressure to half volume. The precipitated solid was filtered off, and the filtrate was further concentrated. The residue was triturated with methanol, and filtered. The filtrate was concentrated partially, and the resulted solution was directly purified by flash chromatography on a silica gel column using dichloromethane - methanol (8:1 to 5:1) as gradient eluents giving 710mg (8.1%) product, which was further treated with methanol giving product 201 with 96% purity. 1HNMR (400 MHz, DMSO-d5); oe 8.06 (s, 1 H), 7.66 (bs, 1 H), 7.32-7.48 (m, 5H), 6.72 (bs, 1 H), 5.81 (d, 1 H, J= 3.6 Hz), 5.37 (m, 1 H), 5.67 (m, 1 H), 4.99 (m, 1 H), 3.97-4.02 (m, 3H), 3.83-3.86 (m, 1 H), 3.50-3.68 (m, 2H); MS (ESI) m/z320 (M + H), 639 (2M + H), 660 (2M + Na). UV, Amax at 202, 232 and 282 nm.
8.1%	With palladium diacetate; potassium carbonate; In water; acetonitrile; at 80℃;	Synthesis of 5-phenyl cytidine 201 : To a stirred solution of <strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong> (200) (1 0.0 g, 27 mol) in 1 00 mL of water and 50 mL acetonitrile was added Pd(Ac)2 (0.58 g, 2.6 mmol), followed by addition of phenyl boronic acid (4.68 g, 38.4 mmol) and potassium carbonate (7.0 g, 50.4 mmol). e resulted reaction mixture was stirred at 80 C overnight and concentrated under reduced ssure to half volume. The precipitated solid was filtered off, and the filtrate was further ncentrate tially, an column usin roduct, which was further treated with methanol giving product 201 with 96% purity.1HNMR (400 Hz, DMSO-d6); delta 8.06 (s, 1 H), 7.66 (bs, 1 H), 7.32-7.48 (m, 5H), 6.72 (bs, 1 H), 5.81 (d, 1 H, J= 3.6 ), 5.37 (m, 1 H), 5.67 (m, 1 H), 4.99 (m, 1 H), 3.97-4.02 (m, 3H), 3.83-3.86 (m, 1 H), 3.50-3.68 (m, ); MS (ESI) m/z 320 (M + H)+, 639 (2M + H)+, 660 (2M + Na)+. UV, Amax at 202, 232 and 282 nm.
710 mg	With palladium diacetate; In water; acetonitrile; at 80℃;Alkaline conditions;	Synthesis of 5-phenyl cytidine 201: To a stirred solution of <strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong> (200)(10.0 g, 27 mmol) in 100 mL ofwater and 50 mL acetonitrile was added Pd(Ac)2(0.58 g, 2.6 mmol), followed by the addition of phenyl boronic acid(4.68 g, 38.4 mmol) and potassium carbonate (7.0 g, 50.4 mmol). The resulted reaction mixture was stirred at 80 Covernight and concentrated under reduced pressure to half volume. The precipitated solid was filtered off, and the filtratewas further concentrated. The residue was triturated with methanol, and filtered. The filtrate was concentrated partially,and the resulted solution was directly purified by flash chromatography on a silica gel column using dichloromethanemethanol (8:1 to 5:1) as gradient eluents giving 710 mg (8.1 %) product, which was further treated with methanol givingproduct 201with 96% purity. 1HNMR (400 MHz, DMSO-d6); delta8.06 (s, 1 H), 7.66 (bs, 1 H), 7.32-7.48 (m, 5H), 6.72 (bs,1 H), 5.81 (d, 1 H, J= 3.6 Hz), 5.37 (m, 1 H), 5.67 (m, 1 H), 4.99 (m, 1 H), 3.97-4.02 (m, 3H), 3.83-3.86 (m, 1 H), 3.50-3.68(m, 2H); MS (ESI) m/z320 (M + H)+, 639 (2M + H)+, 660 (2M + Na)+. UV, lambdamax at 202, 232 and 282 nm

Reference： [1]Patent: WO2015/196130,2015,A2 .Location in patent: Page/Page column 635; 636
[2]Patent: WO2015/196128,2015,A2 .Location in patent: Page/Page column 643; 644
[3]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2221; 2223

36
[ 1147-23-5 ]
5-ethynyl-cytidine tetrakis(triethylammonium) salt [ No CAS ]

Reference： [1]Patent: WO2015/196128,2015,A2
[2]Patent: EP2918275,2015,A1

37
[ 1147-23-5 ]
5-phenyl-CTP tetrakis(triethylammonium) salt [ No CAS ]

Reference： [1]Patent: WO2015/196128,2015,A2
[2]Patent: EP2918275,2015,A1

38
[ 1147-23-5 ]
C₁₁H₁₂Cl₂N₃O₆P [ No CAS ]

Reference： [1]Patent: EP2918275,2015,A1

39
[ 1147-23-5 ]
C₁₁H₁₄N₃O₁₃P₃ [ No CAS ]

Reference： [1]Patent: EP2918275,2015,A1

40
[ 1147-23-5 ]
C₁₅H₁₆Cl₂N₃O₆P [ No CAS ]

Reference： [1]Patent: EP2918275,2015,A1

41
[ 1147-23-5 ]
C₁₅H₁₈N₃O₁₃P₃ [ No CAS ]

Reference： [1]Patent: EP2918275,2015,A1

42
[ 766-98-3 ]
[ 1147-23-5 ]
C₁₇H₁₆FN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50 - 80℃;Inert atmosphere;	<strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong> (0.48 g, 2 mol) was added to 100 ml of the reaction tube under nitrogen atmosphere,4-fluorophenylacetylene (0.36 g, 3 mol),Bis triphenylphosphine palladium dichloride (0.03g, 0.1mmol),Cuprous iodide (0.03 g, 0.12 mmol), 35 ml of triethylamine and 15 ml of N, N-dimethylformamide were reacted at 50 to 80 C for 6 to 10 hours.The solvent was removed in vacuo, diluted with 30 ml of methanol, and the insoluble solid was removed by filtration. Silica gel was added and the solvent was removed by rotary evaporation. The solvent was washed with methanol / methylene chloride to give 0.35 g of nucleoside derivative 2 (brownish solid) For 73%.

Reference： [1]Patent: CN106674316,2017,A .Location in patent: Paragraph 0023-0024

43
[ 766-96-1 ]
[ 1147-23-5 ]
C₁₇H₁₆BrN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50 - 80℃;Inert atmosphere;	<strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong>(0.48 g, 2 mol) was added to 100 ml of the reaction tube under nitrogen atmosphere,4-bromophenylacetylene (0.54 g 3 mol),Bis triphenylphosphine palladium dichloride (0.03g, 0.1mmol),Cuprous iodide (0.03 g, 0.12 mmol), 40 ml of triethylamine and 15 ml of N, N-dimethylformamide were reacted at 50 to 80 C for 6 to 10 hours. The solvent was removed in vacuo, diluted with 30 ml of methanol, and the insoluble solid was removed by filtration. Silica gel was added and the solvent was removed by rotary evaporation. The solvent was removed by methanol / dichloromethane mixed solvent to give 0.41 g of nucleoside derivative 3 (yellow solid) in a yield of 86%.

Reference： [1]Patent: CN106674316,2017,A .Location in patent: Paragraph 0025-0026

44
None [ No CAS ]
[ 1147-23-5 ]
C₁₇H₁₆Gh*N₃O₅ [ No CAS ]

Reference： [1]Patent: CN106674316,2017,A .Location in patent: Page/Page column 2

45
[ 1147-23-5 ]
[ 768-60-5 ]
C₁₈H₁₉N₃O₆ [ No CAS ]