115899-38-2|N-(3-(4-Amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-5-yl)prop-2-yn-1-yl)-2,2,2-trifluoroacetamide| Ambeed

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Quality Control of [ 115899-38-2 ] Purity: 97% SDS Specification

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Product Details of [ 115899-38-2 ]

CAS No. :	115899-38-2
Formula :	C₁₄H₁₅F₃N₄O₅
M.W :	376.29
SMILES Code :	OC[C@@H]1[C@H](C[C@H](N2C(N=C(C(C#CCNC(C(F)(F)F)=O)=C2)N)=O)O1)O
MDL No. :	MFCD28134647
InChI Key :	OKLUSVKQOCPUNW-IVZWLZJFSA-N
Pubchem ID :	14768553

Safety of [ 115899-38-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 115899-38-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	26
Num. arom. heavy atoms	6
Fraction Csp3	0.5
Num. rotatable bonds	5
Num. H-bond acceptors	9.0
Num. H-bond donors	4.0
Molar Refractivity	80.23
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	139.7 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.15
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-1.14
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.48
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-1.44
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.45

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.3
Solubility	19.1 mg/ml ; 0.0506 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.3
Solubility	18.8 mg/ml ; 0.0499 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.1
Solubility	29.5 mg/ml ; 0.0785 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-9.4 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	4.24

Application In Synthesis of [ 115899-38-2 ]

* 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.

Downstream synthetic route of [ 115899-38-2 ]

[ 115899-38-2 ] Synthesis Path-Downstream 1~30

1
[ 115899-38-2 ]
N-{(Z)-3-[4-Amino-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-allyl}-2,2,2-trifluoro-acetamide [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 267 - 270.

2
[ 14719-21-2 ]
[ 611-53-0 ]
[ 115899-38-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;Inert atmosphere; Darkness;	To a solution of 5-iodo-2'-deoxycytidine (10 g, 28.32 mmol) in DMF (200 ml) in a light protected round bottom flask under Argon atmosphere, was added CuI (1.08 g, 5.67 mmol), triethylamine (7.80 ml, 55.60 mmol), 2,2,2-trifluoro-N-prop-2-ynyl-acetamide (12.8 g, 84.76 mmol) and at last Pd(PPh)3)4 (3.27 g, 2.83 mmol). After 18 hours at room temperature, dowex bicarbonate (20 mg) was added and the mixture was stirred for a further 1 h. Filtration and evaporation of the volatiles under reduced pressure gave a residue that was purified by flash chromatography on silica gel (CH2Cl2, CH2Cl2:EtOAc 1:1, EtOAc:MeOH 9:1) .The expected product (7) was obtained as a beige solid in quantitative yield. 1H NMR (D2O) δ 2.24-2.17 (m, 1H, H-2'), 2.41-2.37 (m, 1H, H-2'), 3.68 (dd, J = 12.5, 5.0 Hz, 1H, H-5'), 3.77 (dd, J = 12.5, 3.2 Hz, 1H, H-5'), 3.99 (m, 1H, H-4'), 4.27 (s, 2H, CH2N), 4.34 (m, 1H, H-3'), 6.11 (t, J = 6.3 Hz, 1H, H-1'), 8.1 (br s, 1H, NH) ; MS (ES) : m/z (%) (M-H) 375 (100).
79%		To a solution of 5-iodocytidine C (7.5g, 21.2 mmol) in anhyd DMF (75 mL) CuT (0.30 g,1.57 mmol0 and Pd(PPh3)4 (0.62g, 0.053 mmol) were added. After stirring for 10 mm. triethylamine (6.0 mL, 42.9 mmol) and trifluoro-N-prop-2-ynyl-acetamide (9.6 g, 63.5 mmol) were added. The reaction mixture was stirred overnight at room temperature. All the volatiles were removed under vacuum and the residue was purified by flash chromatography on silica gel (EtOAc/MeOH (0-15%)j to afford the desired product 35 as yellow solid 7.8g (79%). 1H-NMR (DMSo-d6) 9.97 (brs, 1H, NH), 8.15 (s, 1H, H-6), 6.08-6. 12 (t, I = 6.4 Hz, 1H, H-i’), 5.20- 5.21 (d, I = 4 Hz, 1H, OHO, 5.05-5.07 (t, I = 4.8 Hz, 1H, OH), 4.28-4.29 (d, I = 5.2 Hz, 2H, NCH2), 4.15-4.19 (m, 1H, H-3’), 3.77-3.79 (m, 1H, H-4’), 2.11-2.16 (m, 1H, (H-2’), 1.92-1.96 (m, 1H, H-2’).
61%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	Add to a single mouth bottle.dU-I (0.7 mmol, 247 mg),Weigh 9.7mgCuI and 20.3mg Pd (PPh3) 4 added to the reaction flask, evacuated, nitrogen protection, aluminum foil, add 2.3ml DMF, stirred to dissolve, add 0.2ml TEA, weighed F2 (254mg, 1.7mmol) with DMF dissolved in the above reaction flask was added, stirred at room temperature, the reaction overnight. TLC plate monitoring, EA as developing solvent, Rf = 0.35 as the raw material F1, Rf = 0.32 for the product F3, two very close position. After the reaction was over, the solvent was evaporated to dryness under reduced pressure and directly separated by column chromatography. Elution with 20: 1 DCM: MeOH as eluant gave F3214 mg, 61% yield.

58%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In methanol; N,N-dimethyl-formamide; at 20℃;	DC-I, 5-iodo-2'-deoxycytidine (0.70 mmol, 248 mg) was added to a one-necked flask and 10 mg of CuI (25.2 μmol) and 20 mg of Pd (PPh 3) 4 (17.6 μmol) In, evacuated, nitrogen protection, aluminum foil wrapped, add 1.5ml DMF, stirred to dissolve, add 0.2ml TEA,Weigh F2 (254mg, 1.68mmol) dissolved in 1ml DMF was added to the above reaction flask, stirred at room temperature, the reaction overnight. The solvent was spun off, and DCM: MeOH = 5: 1 was used as developing solvent. The residue was purified by TLC to give 153 mg, yield 58%.
3.84 g (102%)	In methanol; dichloromethane;	B. Preparation of 5-(3-Trifluoroacetamido-1-propynyl)-2'-deoxycytidine (56) Iodide 55 (353.1 mg, 1.00 mmol) was coupled for 4 h to N-propargyltrifluoroacetamide following the general procedure given in Example 1C. Chomatography of the crude product with a 0-20% methanol in dichloromethane gradient afforded 3.84 g (102%) of white powder after vacuum drying overnight. This material was homogeneous by TLC, but tenaciously retained solvent. Recrystallization of this powder from boiling isopropanol (10 mL) and cooling to -20 afforded 299.6 mg (74%) alkynylamino nucleoside 56 as white needles (mp 168-170). NMR showed that the recrystallized product was homogeneous and that the crystals contained 0.5 molecules of isopropanol per molecule of product 56.
3.84 g, (102%)	In methanol; dichloromethane;	B. PREPARATION OF 5-(3-TRIFLUOROACETAMIDO1-PROPYNYL)2'-DEOXYCYTIDINE (56) Iodide 55 (353.1 mg, 1.00 mmol) was coupled for 4 h to N-propargyltrifluoroacetamide following the general procedure given in EXAMPLE 1C. Chomatography of the crude product with a 0-20% methanol in dichloromethane gradient afforded 3.84 g, (102%) of white powder after vacuum drying overnight. This material was homogeneous by TLC, but tenaciously retained solvent. Recrystallization of this powder from boiling isopropanol (10 mL) and cooling to -20 afforded 299.6 mg (74%) alkynylamino nucleoside 56 as white needles (mp 168-170). NMR showed that the recrystallized product was homogeneous and that the crystals contained 0.5 molecules of isopropanol per molecule of product 56.

References: [1]Patent: EP2607369,2015,B1 .Location in patent: Paragraph 0138.
[2]Chemical Communications,2005,p. 4551 - 4553.
[3]Patent: WO2016/182984,2016,A1 .Location in patent: Paragraph 00140.
[4]Journal of the American Chemical Society,2005,vol. 127,p. 15071 - 15082.
[5]Patent: CN104693258,2017,B .Location in patent: Paragraph 0088; 0094; 0095.
[6]Patent: CN104292117,2016,B .Location in patent: Paragraph 0443; 0452; 0455; 0456.
[7]Patent: US5151507,1992,A .
[8]Patent: US5047519,1991,A .
[9]Patent: WO2020/146397,2020,A1 .Location in patent: Paragraph 0768.

3
[ 115899-38-2 ]
C₁₄H₁₈F₃N₄O₁₄P₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 15071 - 15082.
[2]Patent: CN104292117,2016,B .

4
[ 115899-38-2 ]
5-[3-aminoprop-1-ynyl]-2'-deoxycytidine-5'-O-triphosphate [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 15071 - 15082.

5
[ 115899-38-2 ]
N-{3-[4-Amino-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-propyl}-2,2,2-trifluoro-acetamide [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 267 - 270.

6
[ 18162-48-6 ]
[ 115899-38-2 ]
5'-O-(tert-butyldimethylsilyl)-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With 1H-imidazole; In N,N-dimethyl-formamide; at 0℃; for 3h;	To a solution of the starting material (7) (1.0 g, 2.66 mmol) and imidazole (200 mg, 2.93 mmol) in DMF (3.0 ml) at 0 C, was slowly added TBDMSC1 (442 mg, 2.93 mmol) in four portions over 1 h. After 2 h, the volatiles were evaporated under reduced pressure and the residue was adsorbed on silica gel and purified by flash chromatography (EtOAc, EtOAc:MeOH 9.5:0.5). The expected product (8) was isolated as a crystalline solid (826 mg, 64%). 1H NMR (d6 DMSO) δ 0.00 (s, 1H, CH3); 0.01 (s, 1H, CH3), 0.79 (s, 9 H, tBu), 1.87-1.80 (m, 1H, H-2'), 2.12 (ddd, J = 13.0, 5.8 and 3.0 Hz, 1H, H-2'), 3.65 (dd, J = 11.5, 2.9 Hz, 1H, H-5'), 3.74 (dd, J = 11.5, 2.5 Hz, 1H, H-5'), 3.81-3.80 (m, 1H, H-4'), 4.10-4.09 (m, 1H, H-3'), 4.17 (d, 2H, J = 5.1 Hz, NCH2), 5.19 (d, 1H, J = 4.0 Hz, 3'-OH), 6.04 (t, J = 6.6 Hz, 1H, H-1'), 6.83 (br s, 1H, NHH), 7.78 (br s, 1H, NHH), 7.90 (s, 1H, H-6), 9.86 (t, J = 5.1 Hz, 1H, -H2CNH) ; MS (ES) : m/z (%) (MH)+ 491 (40%).

References: [1]Patent: EP2607369,2015,B1 .Location in patent: Paragraph 0139.

7
[ 115899-38-2 ]
4-N-acetyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(methylthiolmethyl)-5-[3-(2,2,2-trifluoroacetamide)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: EP2607369,2015,B1 .

8
[ 115899-38-2 ]
4-N-acetyl-3'-O-(azidomethyl)-5'-O-(tert-butyldimethylsilyl)-5-[3-(2,2,2-trifluoroacetamide)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: EP2607369,2015,B1 .

9
[ 115899-38-2 ]
3'-O-(azidomethyl)-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]
4-N-acetyl-3'-O-(azidomethyl)-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: EP2607369,2015,B1 .

10
[ 115899-38-2 ]
4-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: EP2607369,2015,B1 .

11
[ 115899-38-2 ]
4-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-methylthiomethyl-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: EP2607369,2015,B1 .

12
[ 115899-38-2 ]
4-N-benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-azidomethyl-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: EP2607369,2015,B1 .

13
[ 115899-38-2 ]
4-N-benzoyl-3'-O-azidomethyl-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: EP2607369,2015,B1 .

14
[ 58479-61-1 ]
[ 115899-38-2 ]
5'-O-tert-butyldiphenylsilyl-5-[3-(2,2,2-trifluoroacetamido)prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With pyridine; at 0 - 20℃;Inert atmosphere;	Tert-butyldiphenylsilyl chloride (6.97 mL, 26.65 mmol) was added dropwise to a stirred solution of compound 35 (9.11 g, 24.23 mmmol) in dry pyridine (100 mL) at 0 C under N2. After 10 minutes, the solution was allowed to rise to room temperature and stirred overnight. The volatiles were removed under vacuum and the residue was purified by flash chromatography on silica using ethyl acetate in hexanes from 75-100% to afford the desired product 36 (8.42 g, 57%). 1H-NMR (DMSO-d6) 7.95 (s, 1H, H-6), 7.61-7.65 (m, 4H, Ar-H), 7.43-7.47 (m, 6H, Ar-H), 6.11-6.15 (t, J= 6.8 Hz, H-i’), 5.26-5.28 (m, 1H, OH), 4.20-4.27 (m,1H, H-3’), 4.13-4.15 (d, J= 4.8 Hz, NCH2), 3.84-3.90 (m, 3H, H-4 and CH2-5’), 3.70-3.74 (m,1H, CH2-5’), 1.00 (s, (H, C(CH3)3)

References: [1]Patent: WO2016/182984,2016,A1 .Location in patent: Paragraph 00142.
[2]Patent: WO2020/146397,2020,A1 .Location in patent: Paragraph 0768.

15
[ 115899-38-2 ]
N-benzoyl-5'-O-tert-butyldiphenylsilyl-5-[3-(2,2,2-trifluoroacetamido)prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: WO2016/182984,2016,A1 .
[2]Patent: WO2020/146397,2020,A1 .

16
[ 115899-38-2 ]
N-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O-methylthiomethyl-5-[3-(2,2,2-trifluoroacetamido)prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: WO2016/182984,2016,A1 .

17
[ 115899-38-2 ]
N-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O-azidomethyl-5-[3-(2,2,2-trifluoroacetamido)prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: WO2016/182984,2016,A1 .

18
[ 115899-38-2 ]
5'-O-tert-butyldiphenylsilyl-3'-O-azidomethyl-5-[3-(amino)prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: WO2016/182984,2016,A1 .

19
[ 115899-38-2 ]
5'-O-tert-butyldiphenylsilyl-3'-O-azidomethyl-5-[3-(2-((N-tertbutoxyamido-ethyl)-2-yl-disulfanyl)ethyloxy-carboxyamido)-prop-1-ynyl]-2'-deoxycytidine [ No CAS ]

References: [1]Patent: WO2016/182984,2016,A1 .

20
[ 115899-38-2 ]
tri-n-butylamine pyrophosphate [ No CAS ]
5-[3-aminoprop-1-ynyl]-2'-deoxycytidine-5'-O-triphosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		he compound dU-I 60 mg (0.16 mmol), tri-n-butylamine pyrophosphate 150 mg(0.32 mmol) and 66 mg (0.32 mmol) of 2-chloro-4H-1,3,2-benzodioxan-4-one were placed in three reaction tubes. The tri-n-butylamine pyrophosphate was dissolved in 0.5mL anhydrous DMF, then add 0.6mL of freshly distilled tri-n-butylamine, and stirred for half an hour. 2-chloro-4H-1,3,2-benzodioxan-4-one was dissolved in 0.5mL of anhydrous DMF, with stirring under stirring through the syringe was added tri-n-butylamine pyrophosphate solution, stirring for half an hour . The mixture was then poured into F3 and stirred for 1.5 h. Add 5 mL of 3% iodine (9: 1 Py / H20) solution. After 4 minutes 4mL water was added and stirred for 2h.Add 0.5mL3M NaCl solution, then add 30mL absolute ethanol, -20 frozen overnight, centrifugation 3200r / min, 25 ) 20min. Decant the supernatant, precipitate, drained the solvent. Then add TEAB solution and concentrated ammonia, followed by stirring at room temperature overnight. The solvent was evaporated to dryness under reduced pressure to give a white solid, giving dUTP (AP3). Analysis was carried out using an analytical PLC under the following conditions: Column: C18, 10 μm, 4.6 × 250 mm; Flow rate: 1 mL / min; Mobile phase: 20 mM triethylamine acetate and CH3CH2OH; UV detector: 254nm. Product peak generation at t = 13.5 min.

References: [1]Patent: CN104693258,2017,B .Location in patent: Paragraph 0088; 0089; 0098; 0099.

21
[ 115899-38-2 ]
[ 937162-92-0 ]
C₁₆H₂₁N₂O₁₄P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%		In a glove box, 51 mg (0.16 mmol) of compound dU-P and 150 mg (0.32 mmol) of tri-n-butylamine pyrophosphate were weighed out, and 2-chloro-4H-1,3,2-benzodioxo- 66 mg (0.32 mmol) of ketone were placed in three reaction tubesin. The tri-n-butylamine pyrophosphate was dissolved in 0.5mL anhydrous DMF, then add 0.6mL of freshly distilled tri-n-butylamine, and stirred for half an hour. 2-chloro-4H-1,3,2-benzodioxan-4-one was dissolved in 0.5mL of anhydrous DMF, with stirring under stirring through the syringe was added tri-n-butylamine pyrophosphate solution, stirring for half an hour . The mixture was then injected into compound F3 and stirred for 1.5 h. Add 5 mL of 3% iodine (9: 1 Py / H20) solution. After 4 minutes 4mL water was added and stirred for 2h. Add 0.5mL 3M NaCl solution, add 30mL absolute ethanol, freeze at -20 overnight, centrifuge (3200r / min, 25 ) 20min. Decant the supernatant, precipitate, drained the solvent. Then add TEAB solution and concentrated ammonia, followed by stirring at room temperature overnight. The solvent was evaporated to dryness under reduced pressure to give a white solid, giving dUTP-NH2. Analytical HPLC analysis, conditions: Column: C18, 10 μm, 4.6 × 250 mm; flow rate: 1 mL / min; flowPhase: 20 mM triethylamine acetate and CH3CH2OH, gradient wash, 0-20% ethanol (35 min); UV detector: 254 nm. Peak product at t = 16.5 min. Preparative HPLC product was isolated 22mg, that dUTP-P, the yield of 24%.

References: [1]Patent: CN104693258,2017,B .Location in patent: Paragraph 0140.

22
C₇H₆O₁₀P₃^(1-) [ No CAS ]
[ 115899-38-2 ]
C₁₄H₁₆F₃N₄O₁₂P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; for 1.5h;	In a glove box, 90 mg (0.24 mmol) of compound dC (AP3), 264 mg (0.48 mmol) of tri-n-butylamine pyrophosphate, -one 90 mg (0.48 mmol) were placed in three reaction tubes.Tri-n-butylamine pyrophosphate was dissolved in 0.75 mL of anhydrous DMF, then 0.9 mL of anhydrous tri-n-butylamine was added and stirred for half an hour.The 2-chloro-4H-1,3,2-benzodioxan-4-one was dissolved in 0.75mL of anhydrous DMF, with stirring under stirring through the syringe was added tri-n-butylamine pyrophosphate solution, stirring for half an hour .The mixture was then poured into 8 and stirred for 1.5 h.Add 4 mL of 3% iodine (9: 1 Py / H20) solution.After 4 minutes 4mL water was added and stirred for 2h.Add 1mL3M NaCl solution, add 35mL absolute ethanol, freeze at -20 overnight, centrifuge (3200r / min, 25 ) 20min.Decant the supernatant, precipitate, drained the solvent. Add 2ml concentrated ammonia and stir at room temperature for 6h.The solvent was discarded under reduced pressure and a brown solid appeared, RP-HPLC analysis [Conditions: Column: C18, 10 μm, 4.6 × 250 mm; Flow rate: 1 mL / min; Mobile phase: 20 mM TEAA and EtOH, gradient, 0% -20% EtOH (35min); UV detector:254 nm], retention time t = 11 min. RP-HPLC separation [Conditions: Column: C18, 5 μm, 9.4 × 250 mm; flow rate: 4 mL / min; mobile phase: 20 mM TEAA and MeOH,UV-Vis detector: 254nm], NaCl / EtOH to remove triethylamine acetate salt to give 42 mg of a white solid in 24.5% yield.

References: [1]Patent: CN104292117,2016,B .Location in patent: Paragraph 0443; 0452; 0457; 0458.

23
[ 115899-38-2 ]
C₄₁H₄₅F₃N₄O₇Si [ No CAS ]