[ CAS No. 73-24-5 ] {[proInfo.proName]}

Name: 73-24-5|Purin-6-amine|98%
Brand: Ambeed
SKU: A205648
Price: 9.0 USD
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Quality Control of [ 73-24-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 73-24-5 ]

SDS Specification

Alternatived Products of [ 73-24-5 ]

Product Details of [ 73-24-5 ]

CAS No. :	73-24-5	MDL No. :	MFCD00041790
Formula :	C₅H₅N₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GFFGJBXGBJISGV-UHFFFAOYSA-N
M.W :	135.13	Pubchem ID :	190
Synonyms :	6-Aminopurine;Vitamin B4;NSC 14666	Chemical Name :	Purin-6-amine

Calculated chemistry of [ 73-24-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	36.09
TPSA :	80.48 Å²

Pharmacokinetics

GI absorption :	High
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) :	-7.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.53
Log Po/w (XLOGP3) :	-0.53
Log Po/w (WLOGP) :	-0.06
Log Po/w (MLOGP) :	-0.82
Log Po/w (SILICOS-IT) :	0.47
Consensus Log Po/w :	-0.08

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.01
Solubility :	13.2 mg/ml ; 0.0977 mol/l
Class :	Very soluble
Log S (Ali) :	-0.69
Solubility :	27.5 mg/ml ; 0.204 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.77
Solubility :	2.27 mg/ml ; 0.0168 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 73-24-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 73-24-5 ]

* 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 [ 73-24-5 ]
Downstream synthetic route of [ 73-24-5 ]

[ 73-24-5 ] Synthesis Path-Upstream 1~6

1
[ 73-24-5 ]
[ 2715-68-6 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 6, p. 1209 - 1221

2
[ 75-03-6 ]
[ 73-24-5 ]
[ 2715-68-6 ]
[ 24309-36-2 ]
[ 43003-87-8 ]

Reference： [1] Australian Journal of Chemistry, 1982, vol. 35, # 3, p. 525 - 534

3
[ 3083-77-0 ]
[ 73-24-5 ]
[ 5536-17-4 ]

Reference： [1] Russian Journal of Bioorganic Chemistry, 2009, vol. 35, # 6, p. 739 - 745

4
[ 73-24-5 ]
[ 15448-47-2 ]
[ 14047-28-0 ]

Yield	Reaction Conditions	Operation in experiment
5.5 g	Stage #1: With sodium hydroxide In water at 100 - 110℃; for 5 h; Stage #2: With ammonium chloride In water at 25℃;	Example: 6 Preparation of 9-[2-(R)-(Hydroxy)propyl]adenine (I) Method-A Sodium hydroxide (3 g) was added to a stirred suspension of adenine (10 g) in water (50 ml) at room temperature, and the reaction mixture was heated to 100-1 10°C. After 5 hrs at this temperature, the reaction mixture was allowed to cool down to 25°C. Ammonium chloride (3.96 g) and 2-(R)- (+) propylene oxide (6.44 g) were added in succession to the reaction mixture at this temperature. The reaction mixture was maintained at this temperature until the reaction was complete as indicated by TLC. The reaction mixture was concentrated under reduced pressure at 55°C to furnish the desired product, contaminated with unidentified polar impurities. The crude material was purified by column chromatography using a solvent system comprising of methanol and dichloromethane (1 : 9) as the eluant to furnish 9-[2-(R)- (hydroxyl)propyl]adenine as a white solid; yield: 5.5 g.

Reference： [1] Patent: WO2016/178162, 2016, A1, . Location in patent: Page/Page column 19

5
[ 73-24-5 ]
[ 16606-55-6 ]
[ 14047-28-0 ]

Reference： [1] Patent: JP2015/164934, 2015, A, . Location in patent: Paragraph 0166; 0167; 0175

6
[ 73-24-5 ]
[ 16606-55-6 ]
[ 14047-28-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 2, p. 579 - 582

[ 73-24-5 ] Synthesis Path-Downstream 1~88

1
[ 49721-45-1 ]
[ 77287-34-4 ]
[ 73-24-5 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 2246

2
[ 73-24-5 ]
[ 68-94-0 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1889,vol. 13,p. 441
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1903,vol. 39,p. 207
[3]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1905,vol. 44,p. 3
[4]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1906,vol. 50,p. 34
[5]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1909,vol. 63,p. 263,267, 268
[6]Chemische Berichte,1885,vol. 18,p. 1928
Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie,1886,vol. 10,p. 258
[7]Journal of Biological Chemistry,1911,vol. 9,p. 136
[8]Journal of Biological Chemistry,1949,vol. 179,p. 763,767
[9]Journal of the American Chemical Society,1952,vol. 74,p. 4274
[10]Archives of Biochemistry,1954,vol. 50,p. 510

3
3-methyladeninium iodide [ No CAS ]
[ 700-00-5 ]
[ 73-24-5 ]
[ 443-72-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1983,vol. 19,p. 2094 - 2099
Zhurnal Organicheskoi Khimii,1983,vol. 19,p. 2395 - 2401

4
1-methyladeninium iodide [ No CAS ]
[ 700-00-5 ]
[ 73-24-5 ]
[ 443-72-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1983,vol. 19,p. 2094 - 2099
Zhurnal Organicheskoi Khimii,1983,vol. 19,p. 2395 - 2401

5
[ 140654-77-9 ]
[ 73-24-5 ]
[ 140654-78-0 ]

Reference： [1]Tetrahedron Asymmetry,1992,vol. 3,p. 193 - 196

6
[ 73-24-5 ]
[ 143191-76-8 ]
Benzoic acid (2S,4S)-4-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1992,vol. 114,p. 7951 - 7953

7
[ 73-24-5 ]
[ 74-88-4 ]
[ 5142-23-4 ]
[ 935-69-3 ]
[ 700-00-5 ]

Reference： [1]Australian Journal of Chemistry,1982,vol. 35,p. 525 - 534

8
[ 127682-77-3 ]
[ 73-24-5 ]
[ 127682-79-5 ]

Reference： [1]Heterocycles,1994,vol. 37,p. 1853 - 1864

9
[ 73-24-5 ]
[ 143191-76-8 ]
[ 151223-87-9 ]

Reference： [1]Heterocycles,1994,vol. 37,p. 1853 - 1864

10
[ 73-24-5 ]
[ 2032-35-1 ]
[ 23485-30-5 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 875 - 882

11
[ 73-24-5 ]
[ 89860-19-5 ]
(3S,4S,5R)-4-(6-Amino-purin-9-yl)-5-dimethoxymethyl-tetrahydro-furan-3-ol [ No CAS ]
[ 136025-01-9 ]

Reference： [1]Bioorganic and medicinal chemistry,1996,vol. 4,p. 609 - 614

12
[ 7647-01-0 ]
[ 56-65-5 ]
[ 3615-55-2 ]
[ 86119-84-8 ]
[ 73-24-5 ]

Reference： [1]Journal of Biological Chemistry,1947,vol. 167,p. 369,370

13
[ 118-29-6 ]
[ 10465-78-8 ]
[ 73-24-5 ]
C₁₂H₁₉N₉O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 2633 - 2636

14
[ 73-24-5 ]
[ 140-88-5 ]
N-(9H-purin-6-yl)-β-alanine ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1217 - 1230

15
4,8-di-tert-butyl-2,10-dimethyl-6-propa-1,2-dienyl-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-oxide [ No CAS ]
[ 73-24-5 ]
9-[2-(4,8-di-tert-butyl-2,10-dimethyl-6-oxo-12H-5,7-dioxa-6λ⁵-phospha-dibenzo[a,d]cycloocten-6-yl)-1-methyl-vinyl]-9H-purin-6-ylamine [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 10152 - 10161

16
r-2-benzyloxymethyl-c,t-1-bromo-c,t-1-bromomethyl-t-fluorocyclopropane [ No CAS ]
[ 73-24-5 ]
c,t-9-[c,t-1-bromo-t-3-fluoro-r-2-(benzyloxymethyl)cyclopropyl]methyl}adenine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6120 - 6128

17
r-2-benzyloxymethyl-1-bromo-1-bromomethyl-c-2-fluorocyclopropane [ No CAS ]
[ 73-24-5 ]
(Z/E)-9-[cis-(3-fluoro-2-benzyloxymethyl)cyclopropylidene]methyl}adenine [ No CAS ]
9-[1-bromo-c-3-fluoro-r-2-(benzyloxymethyl)cyclopropyl]methyl}adenine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6120 - 6128

18
[ 945915-40-2 ]
[ 73-24-5 ]
[ 945915-41-3 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 7165 - 7171

19
[ 946392-57-0 ]
[ 73-24-5 ]
[ 946392-58-1 ]
7-{(1R,2R,3S)-3-benzoyloxymethyl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobut-1-yl}adenine [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 2827 - 2830

20
C₁₁H₂₂NO₆P [ No CAS ]
[ 73-24-5 ]
diethyl [(1'SR,4'RS)-1'-(6-amino-9H-purin-9-yl)-3'-methyl-2'-oxa-3'-azacyclopent-4'-yl]methylphosphonate [ No CAS ]
diethyl [(1'RS,4'RS)-1'-(6-amino-9H-purin-9-yl)-3'-methyl-2'-oxa-3'-azacyclopent-4'-yl]methylphosphonate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3747 - 3750

21
[ 100-44-7 ]
[ 73-24-5 ]
[ 4261-14-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;tetrabutylammomium bromide; In water; benzene; at 80 - 83℃; for 12h;	Example 2: Synthesis of urin-6-ylamine To a suspension of <strong>[73-24-5]adenine</strong> (3 g, 22.22 mmol) in benzene (55.5 mL) was added sodium hydroxide solution (9.8 mL of 10%) followed by the addition of tetra n-butyl ammonium bromide (1.430 g, 4.44 mmol). To the resulting reaction mixture, benzyl chloride (4.21 g, 3.8 mL, 33.3 mmol) was added under constant stirring. The reaction mixture was heated in an oil bath maintained at about 80-83 C for 12 hours. The reaction mixture was cooled to room temperature to yield a crude organic compound, which was purified by column chromatography using methanol : ethyl acetate solvent mixture as an eluent. Yield = 1. 5 g.

Reference： [1]Patent: WO2005/58898,2005,A2 .Location in patent: Page/Page column 33

22
[ 64-18-6 ]
[ 29634-62-6 ]
[ 73-24-5 ]
[ 2687-25-4 ]
[ 1349616-66-5 ]

Yield	Reaction Conditions	Operation in experiment
14%		A mixture of 3-bromo-l-phenylpropane-l,2-dione (1.0 g, 4.42 mmol), <strong>[73-24-5]adenine</strong> (590 mg, 4.42 mmol) and 2,3-diaminotoluene (540 mg, 4.42 mmol) in EtOH (2OmL) was heated at 6O0C for 4 h. After cooling, the reaction mixture was partitioned between EtOAc and water. The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative etaPLC (Method 1) to give the title compound (23 mg, 14%) as an off-white solid. deltaeta (DMSO-d6) 8.46 (s, IH), 7.88-8.05 (m, 4H), 7.59-7.72 (m, 6H), 7.53 (s, IH), 5.94 (s, 2H), 2.74 (s, 3H). LCMS (ES+) 368.2 (M+H)+, RT 2.15 minutes (Method 3).

Reference： [1]Patent: WO2009/81105,2009,A2 .Location in patent: Page/Page column 69

23
[ 64-18-6 ]
[ 1167541-85-6 ]
[ 73-24-5 ]
9-[(2-phenylquinolin-3-yl)methyl]-9H-purin-6-amine formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4%		A mixture of Intermediate 5 (113 mg, 0.37 mmol) and <strong>[73-24-5]adenine</strong> (51 mg, 0.37 mmol) in DMF (4 mL) was sonicated for 40 minutes at 4O0C then stirred at r.t. for 18 h. <n="107"/>More <strong>[73-24-5]adenine</strong> (51 mg, 0.37 mmol) was added and the reaction heated to 800C for 1 h. Purification by preparative HPLC {Method 1) gave the title compound as a pale yellow solid (5 mg, 4%). deltaH (DMSO-d6) 8.00-8.10 (m, 2H), 7.85-7.95 (m, 3H), 7.75-7.85 (m, IH), 7.50-7.70 (m, 5H), 7.20-7.30 (m, 2H), 5.55 (s, 2H). LCMS (ES+) 353.2 (M+H)+, RT 1.94 minutes {Method 3).

Reference： [1]Patent: WO2009/81105,2009,A2 .Location in patent: Page/Page column 105-106

24
[ 1065480-94-5 ]
[ 73-24-5 ]
[ 1167546-53-3 ]

Yield	Reaction Conditions	Operation in experiment
6%	In N,N-dimethyl-formamide; at 80℃; for 1.5h;	A mixture of Intermediate 61 (98 mg, 0.3 mmol) and <strong>[73-24-5]adenine</strong> (81 mg, 0.6 mmol) in DMF (3 mL) was stirred at 8O0C for 90 minutes. Purification by preparative etaPLC {Method 2) gave the title compound as a white solid (6 mg, 6%). deltaeta (DMSO-d6) 8.30 (s, IH), 8.16 (s, IH), 7.66-7.69 (m, IH), 7.55-7.59 (m, IH), 7.26-7.49 (m, 5H), 7.09 (s, IH), 5.53 (br s, 2H), 5.34 (s, 2H), 2.75 (s, 3H), 2.04 (s, 3H). LCMS (ES+) 381.2 (M+H)+, RT 3.37 minutes {Method 4).

Reference： [1]Patent: WO2009/81105,2009,A2 .Location in patent: Page/Page column 106

25
[ 1167541-90-3 ]
[ 73-24-5 ]
[ 1167546-37-3 ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18.5h;sonication;	A mixture of Intermediate 7 (156 mg, 0.5 mmol), <strong>[73-24-5]adenine</strong> (74 mg, 0.55 mmol) and K2CO3 (76 mg, 0.55 mmol) in DMF (4 mL) was sonicated for 30 minutes then stirred at r.t for 18 h. Purification by preparative etaPLC {Method 1) gave the title compound as a white solid (75 mg, 41%). deltaeta (DMSO-d6) 8.02 (s, IH), 7.89 (s, IH), 7.88 (s, IH), 7.75 (d, J 8 Hz, IH), 7.68-7.69 (m, 2H), 7.62 (d, J 8 Hz, IH), 7.42-7.56 (m, 4H), 7.24 (s, 2H), 5.60 (s, 2H), 2.70 (s, 3H). LCMS (ES+) 367.2 (M+H)+, RT 3.27 minutes {Method 4).

Reference： [1]Patent: WO2009/81105,2009,A2 .Location in patent: Page/Page column 105

26
[ 1167541-94-7 ]
[ 73-24-5 ]
[ 1348508-75-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	In N,N-dimethyl-formamide; at 40 - 80℃; for 1.5h;sonication;	A mixture of Intermediate 9 (82 mg, 0.26 mmol) and <strong>[73-24-5]adenine</strong> (70 mg, 0.52 mmol) in DMF (3 mL) was sonicated for 30 minutes at 400C then stirred at 800C for 1 h. Purification by preparative etaPLC (Method 2) gave the title compound as a white solid (40 mg, 42%). deltaeta (DMSOd6) 8.00 (s, IH), 7.70-7.85 (m, 4H), 7.59-7.61 (m, 2H), 7.40-7.48 (m, 2H), 7.15-7.25 (m, 4H), 5.26 (s, 2H), 1.79 (s, 3H). LCMS (ES+) 367.1 (M+H)+, RT 2.41 minutes (Method 4).

Reference： [1]Patent: WO2009/81105,2009,A2 .Location in patent: Page/Page column 107

27
[ 32837-87-9 ]
[ 73-24-5 ]
[ 1218924-50-5 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 1699 - 1705

28
[ 32837-88-0 ]
[ 73-24-5 ]
[ 1218924-51-6 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 1699 - 1705

29
[ 32837-89-1 ]
[ 73-24-5 ]
[ 1218924-53-8 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 1699 - 1705

30
[ 32837-89-1 ]
[ 73-24-5 ]
[ 1218924-55-0 ]
[ 1218924-53-8 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 1699 - 1705

31
[ 32837-90-4 ]
[ 73-24-5 ]
[ 1218924-52-7 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 1699 - 1705

32
[ 77287-34-4 ]
[ 120-73-0 ]
[ 73-24-5 ]
[ 68-94-0 ]

Reference： [1]ChemBioChem,2010,vol. 11,p. 1240-1243+1159

33
[ 77287-34-4 ]
[ 120-73-0 ]
[ 73-24-5 ]
[ 68-94-0 ]
[ 73-40-5 ]

Reference： [1]ChemBioChem,2010,vol. 11,p. 1240-1243+1159

34
[ 1303556-41-3 ]
[ 73-24-5 ]
[ 1303556-44-6 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2011,vol. 54,p. 175 - 179

35
[ 857440-95-0 ]
[ 73-24-5 ]
[ 1365671-70-0 ]
[ 1365671-46-0 ]

Yield	Reaction Conditions	Operation in experiment
24%; 41%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

36
[ 1365671-87-9 ]
[ 73-24-5 ]
[ 1365671-49-3 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

37
[ 1365671-90-4 ]
[ 73-24-5 ]
[ 1365671-52-8 ]
[ 1365671-73-3 ]

Yield	Reaction Conditions	Operation in experiment
26%; 23%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

38
[ 1365671-93-7 ]
[ 73-24-5 ]
[ 1365671-55-1 ]

Yield	Reaction Conditions	Operation in experiment
43%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

39
[ 1365671-96-0 ]
[ 73-24-5 ]
[ 1365671-58-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

40
[ 1365671-99-3 ]
[ 73-24-5 ]
[ 1365671-76-6 ]
[ 1365671-61-9 ]

Yield	Reaction Conditions	Operation in experiment
36%; 41%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

41
[ 1365672-04-3 ]
[ 73-24-5 ]
[ 1365671-64-2 ]
[ 1365671-79-9 ]

Yield	Reaction Conditions	Operation in experiment
54%; 23%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

42
[ 1365672-08-7 ]
[ 73-24-5 ]
[ 1365671-67-5 ]
[ 1365671-82-4 ]

Yield	Reaction Conditions	Operation in experiment
26%; 38%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation;	General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 154 - 162

43
[ 1415634-04-6 ]
[ 73-24-5 ]
[ 1365347-95-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 10 - 20℃;Inert atmosphere;	General procedure: To a dioxane solution (4.5 mL) of 3 (160 mg, 0.417 mmol), purine (0.627 mmol), and triphenylphosphine (164 mg, 0.627 mmol) under argon at 10 C was added dropwise di-isopropylazodicarboxylate (127 mg, 0.627 mmol). After 12 h stirring at room temperature, volatiles were evaporated, and residue was purified by silica gel column chromatography (MeOH/CH2Cl2 2:98) to give pure desired compound.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 126 - 133

44
[ 73-24-5 ]
[ 56287-17-3 ]
[ 20187-82-0 ]
[ 66-22-8 ]

Reference： [1]FEBS Journal,2013,vol. 280,p. 1475 - 1490

45
[ 73-24-5 ]
[ 118072-93-8 ]
zoledronic acid adenine complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water;	Example 8 Preparation of Zoledronic, Adenine, and Water Complex by Solvent-Drop Grinding 96 mg of zoledronic acid is ground with 65 mg of adenine and 60 muL of water is added to the solid mixture. The solids gathered after grinding are stored.

Reference： [1]Patent: US2014/349974,2014,A1 .Location in patent: Paragraph 0077; 0078

46
[ 123-08-0 ]
[ 73-24-5 ]
4-((7H-purin-6-ylimino)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In ethanol; for 6h;Dean-Stark; Reflux;	Schiff base ligand (1) was prepared by taking <strong>[73-24-5]adenine</strong> and Para-hydroxyl benzaldehyde in ethanol and pouring in a three neck round bottom flask equipped with a reflux condenser, thermometer and a Deane-Stark funnel. The above reaction mixture was heated under reflux for 6 h. Water formed during the reaction was removed through Deane-Stark funnel. The solvent was removed under reduced pressure. The resulting white solid was recrystallized from chloroform. Yield: 87%; m.p: 131-133 C; Mol. Formula: C12H9N5O; Mol. wt. 239.23. Elemental analysis: For C12H9N5O, Anal. calcd(%): C, 60.25; H, 3.79; N, 29.27, found (%): C, 59.98; H, 3.74; N,29.20; IR (KBr): 3285br (nu O-H); 3085sr (nu C-H); 2895br (nu N-H); 1565sr (nu C=N). 1H NMR (CDCl3): delta 4.5s (1H, 1 hydroxyl); 6.4m (2H, aromatic); 6.9m (2H, aromatic); 7.4d (1H, Imidazole); 8.8s (1H, Azomethanic); 9.4s (1H, pyrimidinic); 10.2d (1H, Imidazole). 13C NMR (CDCl3): delta C2 = 157.5; C4 = 121.7; C5 = 110.8; C6 = 175.4; C9 = 134.6; C11 = 118.6; C12 = 128.2; C13 = 118.7; C14 = 155.4; C15 = 112.7; C16 = 129.3; C18 = 167.5.

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 767,p. 91 - 100

47
(R)-(((1-chloropropan-2-yl)oxy)methyl)phosphonic acid bis(diethylamide) [ No CAS ]
[ 73-24-5 ]
[ 147127-20-6 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 820 - 823

48
(R)-(((1-chloropropan-2-yl)oxy)methyl)phosphonic acid bis(diethylamide) [ No CAS ]
[ 73-24-5 ]
(2R)-(((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid bis(diethylamide) [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 820 - 823

49
[ 73-24-5 ]
[ 16606-55-6 ]
(R)-3-(2′-hydroxyprop-1-yl)adenine [ No CAS ]
[ 14047-28-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 579 - 582

50
[ 67-56-1 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 127-19-5 ]
[ 121-91-5 ]
[ 71-91-0 ]
[ 73-24-5 ]
(tetraethylammonium)[Cd₃(adenine)2(isophtalate)2bromide]*3methanol*3.5(N,N-dimethylacetamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	at 20 - 100℃; for 72h;	Isophthalic acid (H2ipa, 166 mg,1 mmol), <strong>[73-24-5]adenine</strong> (Had, 135 mg, 1 mmol), Cd(NO3)2 4H2O (462 mg, 1 mmol) and tetraethylammonium bromide (220 mg, 1 mmol)were added to 4 mL DMA (N,N-dimethylacetamide) and 1.5 mL MeOH (methanol)mixed solvents, and then the solution was placed in a 20 mL vial and stired at room temperature for 1h. The mixture was heated at 100 C for 3 days, and then cooled slowly to room temperature over 4h. Colourless rod-like crystals of the product were formed and collected by filtration and washed with DMA several times. (Yield: 65%based on H2ipa).

Reference： [1]Journal of Solid State Chemistry,2016,vol. 238,p. 241 - 245

51
[ 73-24-5 ]
[ 71-00-1 ]
C₁₁H₁₂N₈O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine; In ethanol; chloroform; for 6h;Reflux;	For the synthesis of ligand (L) <strong>[73-24-5]adenine</strong> (0.2 mM) was suspended in chloroform (15 ml) and neutralized with triethylamine. Ethanolic solution of L-histidine (0.2 mM)was added to the above solution and the resultant mixture was refluxed for 6 h. The solid product formed was filtered and washed with chloroform. The filtrate together with the washings were treated with citric acid solution (10 %,10 ml) and with water. The organic layer was separated.After drying over anhydrous CaCl2, the solvent was removed by evaporation to obtain the ligand.

Reference： [1]Journal of Fluorescence,2016,vol. 26,p. 1825 - 1837

52
[ 73-24-5 ]
[ 15448-47-2 ]
[ 14047-28-0 ]

Yield	Reaction Conditions	Operation in experiment
5.5 g		Example: 6 Preparation of 9-[2-(R)-(Hydroxy)propyl]adenine (I) Method-A Sodium hydroxide (3 g) was added to a stirred suspension of adenine (10 g) in water (50 ml) at room temperature, and the reaction mixture was heated to 100-1 10C. After 5 hrs at this temperature, the reaction mixture was allowed to cool down to 25C. Ammonium chloride (3.96 g) and 2-(R)- (+) propylene oxide (6.44 g) were added in succession to the reaction mixture at this temperature. The reaction mixture was maintained at this temperature until the reaction was complete as indicated by TLC. The reaction mixture was concentrated under reduced pressure at 55C to furnish the desired product, contaminated with unidentified polar impurities. The crude material was purified by column chromatography using a solvent system comprising of methanol and dichloromethane (1 : 9) as the eluant to furnish 9-[2-(R)- (hydroxyl)propyl]adenine as a white solid; yield: 5.5 g.

Reference： [1]Patent: WO2016/178162,2016,A1 .Location in patent: Page/Page column 19

53
[ 31618-90-3 ]
[ 73-24-5 ]
[ 15448-47-2 ]
[ 147127-20-6 ]

Yield	Reaction Conditions	Operation in experiment
1.42 g		Example: 11 Preparation of 9-[2-(R)-(phosphonomethoxy)propyl] <strong>[73-24-5]adenine</strong> (II). Method-A Magnesium di-tert-butoxide (51 mg) was added to a stirred suspension of <strong>[73-24-5]adenine</strong> (2 g) in methanol (12 ml) at 10C. After 4 h at this temperature, sodium hydroxide (12 mg) and (R)-(+)-propylene oxide (1 .25 g) were added in succession to the reaction mixture. The reaction mixture was allowed to warm to room temperature and stirred at this temperature until the reaction was complete, as indicated by TLC. Methanol was evaporated under vacuum. N, N-Dimethylformamide (16 ml) was added to the crude reaction mixture thus obtained and the mixture was heated to 60-70C. Magnesium di-tert-butoxide (7 g) was added to the reaction mixture in four divided batches over a period of 15 minutes at this temperature. The mixture was heated to 80-90C, and stirred at this temperature for 30 minutes. Diethyl p-toluenesulfonyloxymethylphosphonate (13.2 g) was added drop by drop to the reaction mixture over a period of 4 h, and the mixture was stirred at this temperature until the reaction was complete, as indicated by TLC. N, N-Dimethylformamide was distilled out under vacuum at 90-100C. Aqueous hydrobromic acid (48% w/w, 30 ml) was then added to the residue and the reaction mixture was heated to gentle reflux. After approximately 20 h at this condition, the reaction mixture was allowed to cool down to room temperature and filtered. The filtered solid was washed with dichloromethane (10 ml). The washing was concentrated to furnish a residue. The residue was combined with the filtrate and the combined filtrate was washed with dichloromethane (2 X 10 ml). To the aqueous layer, an aqueous solution of sodium hydroxide (50 %) was added until the pH attained 2.1 -3. After several hours at room temperature, the aqueous layer was cooled to 0- 5C and stirred at this temperature for further hours to maximize precipitation of the desired product from the solution. The precipitated solid was filtered, washed with cold water (1 X 5 ml), acetone (2X 5 ml) and dried to obtain 9-[2-(R)-(phosphonomethoxy)propyl]<strong>[73-24-5]adenine</strong>; yield: 1 .42 g.

Reference： [1]Patent: WO2016/178162,2016,A1 .Location in patent: Page/Page column 23-24

54
[ 73-24-5 ]
[ 58-96-8 ]
[ 58-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	With purine nucleoside phosphorylase; uridine phosphorylase; In aq. phosphate buffer; at 60℃; for 1.5h;Enzymatic reaction;	Transglycosylation reaction was carried out at analytical scale in the followingconditions: 250 ml of cell lysates (equivalent to 14 units of each UPase and PNPase enzymatic activities) was added to10 ml of a solution having the following composition: 4 mM 1-beta-D-ribofuranosyluracil (uridine nucleoside), 4 mM <strong>[73-24-5]adenine</strong>base, 30 mM potassium phosphate buffer pH 7, thermostatically controlled at 60C. After 1.5 hours at 60C, the reactionwas stopped by diluting the mixture 1:5 and cooling in ice. The percentage of bioconversion of <strong>[73-24-5]adenine</strong> base to 9-beta-Dribofuranosyl<strong>[73-24-5]adenine</strong>(adenosine nucleoside) was determined by analyzing an aliquot of the reaction mixture by highperformance liquid chromatography (HPLC) with the use of Kromasil 100-5C18 (Akzo Nobel) column of a size of 250 x4.6mm and eluted with a 4% methanol-water solution. The transglycosylation catalytic activity was expressed as units· ml -1 (mmoles ofAra-A formed in 1.5 hours · ml -1 of mixture of cell lysates) or in units · g -1 of moist resin (mmoles ofD-ribofuranosyl<strong>[73-24-5]adenine</strong> formed in 1.5 hours · ml -1 of cell lysate) and was calculated relative to a standard D-ribofuranosyl<strong>[73-24-5]adenine</strong>solution eluted by HPLC in the same conditions. Under these conditions, about 55 percent of adenosinenucleoside was formed (approximately 9 units per ml of cell lysate).

Reference： [1]Patent: EP2516637,2016,B1 .Location in patent: Paragraph 0076

55
[ 118-70-7 ]
[ 77287-34-4 ]
[ 73-24-5 ]

Yield	Reaction Conditions	Operation in experiment
81.8%	at 140 - 150℃; for 4h;	10 mL of formamide and 90 g of <strong>[118-70-7]4,5,6-triaminopyrimidine</strong> (Formula 6) were added to a 1000 mL reaction flask and heated to 140 to 150 C for 4 hours. The reaction was completed and cooled to a temperature of 25 to 15 C Crystallization, filtration, formamide rinsing, water elution, gray adipate crude, refined with water, activated carbon decolorization after 79.5g white crystalline powder adenine (Formula 1), yield 81.8%, HPLC 99.9%.
81.8%	at 140 - 150℃; for 4h;	10 mL of formamide and 90 g of <strong>[118-70-7]4,5,6-triaminopyrimidine</strong> (Formula 6) were added to a 1000 mL reaction flask and heated to 140 to 150 C for 4 hours. The reaction was completed and cooled to a temperature of 25 to 15 C for crystallization, filtration, formamide rinsing, water elution, the crude gray adenine, water purification, activated carbon decolorization. 79.5g white crystalline powder adenine (Formula 1), the yield of 81.8%, HPLC 99.9%.

Reference： [1]Patent: CN106749043,2017,A .Location in patent: Paragraph 0023
[2]Patent: CN106749253,2017,A .Location in patent: Paragraph 0017; 0020; 0024

56
[ 96-32-2 ]
[ 73-24-5 ]
[ 23124-10-9 ]

Yield	Reaction Conditions	Operation in experiment
50%		The ester derivative of <strong>[73-24-5]adenine</strong> was synthesized by modified reported procedure [4]. Adenine (3.0 g, 22.20 mmol) was dissolved in dry DMF 50 mL followed by the addition of anhydrous potassium carbonate (1.01 g, 44.40 mmol) under N2 atmosphere at temperature 0 C. After 1 hr, methyl bromoacetate (3.70 mL, 33.0 mmol) was slowly added in to the reaction mixture, the reaction was stirred for 24 hours. The reaction was monitored by thin layer chromatography, solvent was evaporated at 70 0C under reduced pressure and the reaction mixture was purified by the column chromatography. The white powder product was eluted by using 2 % (methanol/DCM). (50 % yield). HRMS: (M+H)+ calculated: 208.0835, observed: 208.0835. 1H NMR: (500 MHz, DMSO-d6, 25 C, TMS) delta (ppm) 3.76 (s, 3H, -OCH3), 4.94 (t, 2H.-CH2-), 6.90 (s, 2H, N6-H), 7.84 (s, 1H, C2-H), 8.05 (s, 1H, C8-H).

Reference： [1]Inorganica Chimica Acta,2019,vol. 484,p. 167 - 173

57
[ 73-24-5 ]
[ 16606-55-6 ]
[ 14047-28-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In N,N-dimethyl-formamide; at 125 - 138℃;	Step 4. (R)-9-[2-(diethylphosphonomethoxy)propyl]adenine: In a reactor containing an inert atmosphere, for example nitrogen, adenine (1.0 kg),A mixture of sodium hydroxide (11.8 g), (R) -1,2-propylene carbonate (0.83 kg), and N, N-dimethylformamide (6.5 kg) was treated with about 0.5% area normalized HPLC, Indicating that the adenine remained unresolved until the reaction was completed,Heat to 130 C (typically about 125-138 C) for about 18-30 hours. The resulting mixture is cooled to about 25 C. (typically about 20 to 30 C.) and contains a Stage I intermediate, (R) -9- (2-hydroxypropyl) adenine, It can precipitate at this point. After cooling, lithium t-butoxide (3.62 kg), 2.0 M in tetrahydrofuran was added to stage I intermediate to produce the lithium salt of (R) -9- (2-hydroxypropyl) adenine in a mild exothermic reaction . The slurry was treated with diethyl p-toluenesulfonyloxymethyl phosphonate (1.19 kg) and the mixture was heated to a temperature of about 32 C. (typically about 30 to 45 C.) and heated for at least about 2 hours (Typically about 2 to 3 hours) Meanwhile, the mixture becomes uniform. Further diethyl p-toluenesulfonyloxymethylphosphonate (1.43 kg) is added and the mixture is heated at a temperature of about 32 C. (typically about 30-45 C.) for at least about 2 hours (typically about 2- 3 hours). Further lithium t-butoxide (0.66 kg), 2.0 M in tetrahydrofuran and diethyl p-toluenesulfonyloxymethylphosphonate (0.48 kg) were added two more times and after each time the mixture was added at a temperature of about 32 C. for at least about 2 hours Stir. Completion of the reaction is monitored by indicating that area normalized HPLC, if necessary, shows only 10% residual Stage I intermediate. If the reaction is incomplete, additional lithium t-butoxide (0.33 kg), 2.0 M in tetrahydrofuran and diethyl p-toluenesulfonyloxymethylphosphonate (0.24 kg) are added and the reaction mixture is heated at a temperature of about 32 C. Maintain reaction completion by maintaining for at least about 2 hours. The mixture is then cooled to about 25 C (typically about 20-40 C) and then glacial acetic acid (0.5 kg) is added. The resulting mixture is concentrated in vacuo at a final maximum mixture temperature of about 80 C., under a vacuum of about 29 inches Hg (in Hg). The residue is cooled to about 50 C. (typically about 40-60 C.) and water (1.8 kg) is added and the reaction is rinsed into additional water (1.8 kg). The solution is continuously extracted with dichloromethane (about 35 kg) for 12 to 48 hours and periodically glacial acetic acid (0.2 kg) is added to the aqueous phase after about 5 hours and about 10 hours after the continuous extraction time. Completion of extraction can be achieved by showing that the area-normalized HPLC shows that the residual amount of (R) -9- [2-diethylphosphonomethoxy) propyl] adenine in the aqueous phase is only about 7% It is confirmed. The combined dichloromethane extracts are first concentrated at atmospheric pressure and then in vacuo at extraction temperature at a temperature of only about 80 C. to give the title compound as a viscous orange oil. The title compound yield is about 40-45% by weight (normalized HPLC) and its purity is typically 60-65% by area normalized HPLC. The actual weight of the title compound after concentration is approximately 1.6 times the stoichiometric amount (ie, 3.8 times the expected yield). The additionally observed weight is due to impurities and / or solvents remaining after continuous extraction and concentration.

Reference： [1]Patent: JP2015/164934,2015,A .Location in patent: Paragraph 0166; 0167; 0175

58
heptadecan-9-yl 8-((3-chloropropyl)(8-(nonyloxy)-8-oxooctyl)amino)octanoate [ No CAS ]
[ 73-24-5 ]
heptadecan-9-yl 8-((3-(6-amino-9H-purin-9-yl)propyl)(8-(nonyloxy)-8-oxooctyl)amino)octanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 90℃; for 16h;Sealed tube;	[00123] A mixture of heptadecan-9-yl 8-((3-chloropropyl)(8-(nonyloxy)-8- oxooctyl)amino)octanoate (500 mg, 0.67 mmol), <strong>[73-24-5]adenine</strong> (135 mg, 1.0 mmol) and 1,8- diazabicycloundec-7-ene (137 mu, 1.0 mmol) in 2 mL DMF was heated at 90 C in a sealed tube for 16 h. The reaction mixture was concentrated to dryness and partitioned between dichloromethane and water. The organic layer was washed with brine. After it was dried over sodium sulfate, the filtrate was concentrated and purified by ISCO (SiC : MeOH/CH2Ch/l% NH4OH 0 to 5%) to afford the product as a yellow oil (325 mg, 57%). LC/UV (202 nm): RT = 8.47 min. MS (APCI): m/z (MH+) 841.7. NMR (300 MHz, CDCb) delta: ppm 8.36 (s, 1H); 7.80 (s, 1H); 5.51 (bs, 2H); 4.85 (p, 1H, J= 6.0 Hz); 4.24 (t, 2H, J= 7.0 Hz); 4.04 (t, 2H, J = 6.6 Hz); 2.45-2.24 (m, 10H); 2.01 (p, 2H, J= 6.9 Hz); 1.68-1.17 (m, 62H); 0.86 (m, 9H).

Reference： [1]Patent: WO2018/170306,2018,A1 .Location in patent: Paragraph 00123

59
[ 55368-24-6 ]
[ 73-24-5 ]
[ 432016-77-8 ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

60
[ 1016495-38-7 ]
[ 73-24-5 ]
C₁₅H₁₅N₅O₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

61
C₁₀H₁₀BrClO₂ [ No CAS ]
[ 73-24-5 ]
C₁₅H₁₄ClN₅O₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

62
C₁₁H₁₂BrNO₃ [ No CAS ]
[ 73-24-5 ]
C₁₆H₁₆N₆O₃ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

63
[ 1189816-63-4 ]
[ 73-24-5 ]
C₁₅H₁₄BrN₅O₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

64
1-(2-bromoethoxy)-2-(trifluoromethoxy)benzene [ No CAS ]
[ 73-24-5 ]
C₁₄H₁₂F₃N₅O₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

65
C₁₀H₈BrF₃O₂ [ No CAS ]
[ 73-24-5 ]
C₁₅H₁₂F₃N₅O₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

66
[ 3524-86-5 ]
[ 73-24-5 ]
C₁₇H₁₉N₅O₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 92,p. 1998 - 2008

67
[ 103-76-4 ]
[ 73-24-5 ]
[ 302964-08-5 ]
dasatinib adenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a 500 mL glass vessel equipped with a stirrer, condenser and a thermometer probe were added the Formula II (10.0 g, 0.0254 mol, 1.00 equiv.), Formula III (30.0 mL, 3.00 vol) and N, N-dimethyl acetamide (10.0 mL, 1.00 vol) and the mass was heated to 75±5 C. The reaction mass was maintained at 75±5 C under stirring. The reaction mass was cooled to 25±5 C and Adenine (5.14 g, 0.038 mol, 1.50 equiv.) was added to the reaction mass at 25±5 C under stirring. Methanol (300 mL, 30.0 vol) was added to the reaction mass at constant rate at 25±5 C under stirring. The mass was heated to 60±2 C and the resulting suspension was maintained at the same temperature under stirring. The mass was cooled to 25±5 C and maintained at the same temperature. Water (130 mL, 13.0 vol) was added to the reaction mass at a constant rate under stirring. The reaction mass was maintained at 25±5 C. The mass was filtered and the solid was washed with Methanol (70.0 mL, 7.00 vol), suck dried and dried at 50±5 C under vacuum to obtain Dasatinib-Adenine co-crystal of Formula lb as a crystalline solid.

Reference： [1]Patent: WO2019/8555,2019,A1 .Location in patent: Paragraph 67; 68; 69

68
3'-(1-((ethoxy(hydroxy)phosphoryl)methyl)-1H-imidazol-4-yl)-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
[ 73-24-5 ]
sodium ethyl [(4-{3'-[(9H-purin-6-yl)carbamoyl]-[1,1'-biphenyl]-3-yl}-1H-imidazol-1-yl)methyl]phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With dmap; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	General procedure: To a stirred solutionof carboxylic acid 17 (1.42 mmol) in DMF (13 mL) was added underargon N,N0-carbonyldiimidazole (1.5 eq.), N,N-dimethyl-4-aminopyridine (0.2 eq.), <strong>[73-24-5]adenine</strong> or 2a (1.5 eq.). The reactionmixture was stirred at 100 C until the starting material disappeared(checked by HPLC). Solvent was removed under reducedpressure and column chromatography of the crude materials onreverse phase (RP18, gradient: water to acetonitrile 100%) gave theexpected ethylphosphonate which was passed through a DowexNa ion exchange column. The desired fractions were collected andfreeze dried leading to the desired compounds 18 or 19 as sodiumsalt. 4.5.3.8. Sodium ethyl ((4-(3'-((7H-purin-6-yl)carbamoyl)-[1,1'-biphenyl]-3-yl)-1H-imidazol-1-yl) methyl) phosphonate (18).Yield 63%; 1H NMR (DMSO-d6): d 1.03 (t, J 7 Hz, 3H), 3.65 (q,J 7 Hz, 2H), 3.89 (d, J 12 Hz, 2H), 7.40e8.47 (m,10H), 8.53 (s, 1H),8.75 (s, 1H), 11.80 (bs, 1H), 12.5 (bs, 1H); 13C NMR (DMSO-d6): delta 16.9 (d, 3J 6 Hz), 44.7 (d, 1J 137 Hz), 59.2 (d, 2J 5.7 Hz),117.5, 122.5, 123.7, 124.5, 126.0, 127.6, 129.2, 130.8, 135.8, 139.1,139.5, 140.5, 146.1, 151.2, 166.5; 31P NMR (DMSO-d6): delta 8.35; MS(ESI) m/z 504 [M-Na2H]; HRMS: calcd for C24H23N7O4P [MNa2H] 504.1468, found 504.1549.