[ CAS No. 2715-70-0 ]

Name: 2715-70-0|9-Butyl-9H-purin-6-amine|97%
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SKU: A129540
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Quality Control of [ 2715-70-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 2715-70-0 ]

CAS No. :	2715-70-0	MDL No. :	MFCD18843695
Formula :	C₉H₁₃N₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BKXMJMZKKNIYRD-UHFFFAOYSA-N
M.W :	191.23 g/mol	Pubchem ID :	75929
Synonyms :

Calculated chemistry of [ 2715-70-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.44
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	55.41
TPSA :	69.62 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	1.25
Log Po/w (WLOGP) :	1.22
Log Po/w (MLOGP) :	0.56
Log Po/w (SILICOS-IT) :	0.64
Consensus Log Po/w :	1.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.09
Solubility :	1.55 mg/ml ; 0.00811 mol/l
Class :	Soluble
Log S (Ali) :	-2.31
Solubility :	0.936 mg/ml ; 0.00489 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.59
Solubility :	0.496 mg/ml ; 0.00259 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 2715-70-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2715-70-0 ]

* 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 [ 2715-70-0 ]

[ 2715-70-0 ] Synthesis Path-Downstream 1~47

1
[ 5444-83-7 ]
[ 2715-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; ammonia

Reference： [1]Montgomery; Temple [Journal of the American Chemical Society, 1958, vol. 80, p. 409]

2
[ 2715-70-0 ]
[ 75-36-5 ]
N⁶-acetyl-9-butyladenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With pyridine In dichloromethane for 2h; Ambient temperature;

Reference： [1]Nowick, James S.; Chen, Jenny S.; Noronha, Glenn [Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7636 - 7644]

3
[ 109-65-9 ]
[ 134461-75-9 ]
[ 2715-70-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;
85%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;
85%	With potassium carbonate In N,N-dimethyl-formamide

81%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 96h; Inert atmosphere;
64%	Stage #1: adenine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-butane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	4.1.1.1 General procedure used for preparing 9-alkylated adenine General procedure: To a suspension of adenine in dry DMF, NaH (1.1equiv) was added under argon. The mixture was stirred at rt for 1h then the alkylating agent (1.05equiv) was added and the mixture was stirred until complete reaction.
	With sodium hydride 1.) DMF, 1 h, 2.) DMF, 16 h; Yield given. Multistep reaction;
	With potassium carbonate In dimethyl sulfoxide at 23℃; for 48h;	2.7 Synthesis of n-butyl adenine (nBA) guest molecule Adenine (6.05 g, 44.8 mmol), 1-bromobutane (6.16 g, 45.0 mmol), potassium carbonate (8.33 g, 60.3 mmol), and DMSO (60 mL) were added to a 250-mL round-bottomed flask. The resulting solution was stirred for 48 h at 23 °C and then poured into 600 mL water. The aqueous solution was extracted three times with 100 mL DCM and then the organic layer was washed three times with 100 mL water. The organic layer was dried over magnesium sulfate and concentrated in vacuo to obtain a solid. The product was obtained as a white solid after recrystallization from chloroform:hexanes. 1H NMR (400 MHz, CDCl3): 0.96 ppm (t, 3H, Ha), 1.37 ppm (m, 2H, Hb), 1.88 ppm (p, 2H, Hc), 4.20 ppm (t, 2H, Hd), 5.67 ppm (s, 2H, He), 7.79 ppm (s, 1H, Hf), 8.37 ppm (s, 1H, Hg) (Fig. S5).

Reference： [1]Ghosh, Kumaresh; Sen, Tanushree; Fröhlich, Roland [Tetrahedron Letters, 2007, vol. 48, # 39, p. 7022 - 7026]
[2]Location in patent: scheme or table Ghosh, Kumaresh; Sen, Tanushree [Tetrahedron Letters, 2008, vol. 49, # 50, p. 7204 - 7208]
[3]Location in patent: scheme or table Ghosh, Kumaresh; Sen, Tanushree [Beilstein Journal of Organic Chemistry, 2010, vol. 6]
[4]Location in patent: experimental part Lambertucci, Catia; Antonini, Ippolito; Buccioni, Michela; Dal Ben, Diego; Kachare, Dhuldeo D.; Volpini, Rosaria; Klotz, Karl-Norbert; Cristalli, Gloria [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 7, p. 2812 - 2822]
[5]Boucherle, Benjamin; Bertrand, Johanna; Maurin, Bruno; Renard, Brice-Loïc; Fortuné, Antoine; Tremblier, Brice; Becq, Frédéric; Norez, Caroline; Décout, Jean-Luc [European Journal of Medicinal Chemistry, 2014, vol. 83, p. 455 - 465]
[6]Nowick, James S.; Chen, Jenny S.; Noronha, Glenn [Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7636 - 7644]
[7]Tamami, Mana; Hemp, Sean T.; Zhang, Keren; Zhang, Mingqiang; Moore, Robert B.; Long, Timothy E. [Polymer, 2013, vol. 54, # 6, p. 1588 - 1595]

4
[ 2715-70-0 ]
C₉H₁₁ClN₅^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tert-butylhypochlorite In methanol

Reference： [1]Dress, K. Ruprecht; Goossen, Lukas J.; Liu, Hong; Jerina, Donald M.; Sharpless, K. Barry [Tetrahedron Letters, 1998, vol. 39, # 42, p. 7669 - 7672]

5
[ 2715-70-0 ]
[ 98-88-4 ]
N₁-(9-butyl-9H-6-purinyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In pyridine at 100℃; for 1h;

Reference： [1]Crisp, Geoffrey T.; Jiang, Yu-Lin [Tetrahedron, 1999, vol. 55, # 2, p. 549 - 560]

6
[ 2715-70-0 ]
[ 173314-95-9 ]
4-butoxy-N₂,N₆-di(9-butyl-9H-6-purinyl)-2,6-pyridinedicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride 1.) reflux, 0.5 h, 2.) pyridine, 90 deg C, 1 h; Yield given; Multistep reaction;

Reference： [1]Crisp, Geoffrey T.; Jiang, Yu-Lin [Tetrahedron, 1999, vol. 55, # 2, p. 549 - 560]

8
[ 2715-70-0 ]
[ 202136-43-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With bromine; sodium acetate; acetic acid In tetrahydrofuran; methanol at 20℃; for 0.5h;
41%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 40h; Inert atmosphere;

Reference： [1]Zhang, Lin; Fan, Junhua; Vu, Khang; Hong, Kevin; Le Brazidec, Jean-Yves; Shi, Jiandong; Biamonte, Marco; Busch, David J.; Lough, Rachel E.; Grecko, Roy; Ran, Yingqing; Sensintaffar, John L.; Kamal, Adeela; Lundgren, Karen; Burrows, Francis J.; Mansfield, Robert; Timony, Gregg A.; Ulm, Edgar H.; Kasibhatla, Srinivas R.; Boehm, Marcus F. [Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5352 - 5362]
[2]Location in patent: experimental part Lambertucci, Catia; Antonini, Ippolito; Buccioni, Michela; Dal Ben, Diego; Kachare, Dhuldeo D.; Volpini, Rosaria; Klotz, Karl-Norbert; Cristalli, Gloria [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 7, p. 2812 - 2822]

9
[ 134461-75-9 ]
[ 2715-70-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With caesium carbonate In N,N-dimethyl-formamide for 16h;

10
[ 2715-70-0 ]
[ 10387-13-0 ]
C₃₄H₃₆N₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	Stage #1: 9-butyladenine With sodium hydride In tetrahydrofuran for 3h; Heating; Stage #2: 9,1-bis(chloromethyl)anthracene In tetrahydrofuran for 10h; Further stages.;

Reference： [1]Ghosh, Kumaresh; Sen, Tanushree; Fröhlich, Roland [Tetrahedron Letters, 2007, vol. 48, # 39, p. 7022 - 7026]

11
[ 2715-70-0 ]
[ 24463-19-2 ]
C₂₄H₂₃N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 9-butyladenine With sodium hydride In tetrahydrofuran for 3h; Heating; Stage #2: anthracenylmethyl chloride In tetrahydrofuran for 6h; Heating; Further stages.;
60%	With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide Reflux;

12
[ 2715-70-0 ]
8-(benzothiazol-2-ylsulfanyl)-9-butyl-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 78 percent / dimethylformamide / 6 h / 130 °C

13
[ 2715-70-0 ]
9-butyl-8-(7-chlorothiazolo[4,5-c]pyridin-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 86 percent / dimethylformamide / 6 h / 130 °C

14
[ 2715-70-0 ]
9-butyl-8-(6-chlorobenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 77 percent / dimethylformamide / 6 h / 130 °C

15
[ 2715-70-0 ]
9-butyl-8-(4-chlorobenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 72 percent / dimethylformamide / 6 h / 130 °C

16
[ 2715-70-0 ]
9-butyl-8-(5-chlorobenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 75 percent / dimethylformamide / 6 h / 130 °C

17
[ 2715-70-0 ]
9-butyl-8-(7-fluorobenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 73 percent / dimethylformamide / 6 h / 130 °C

18
[ 2715-70-0 ]
9-butyl-8-(7-methylbenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 79 percent / dimethylformamide / 6 h / 130 °C

19
[ 2715-70-0 ]
8-(7-bromobenzothiazol-2-ylsulfanyl)-9-butyl-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 80 percent / dimethylformamide / 6 h / 130 °C

20
[ 2715-70-0 ]
9-butyl-8-(7-chlorobenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 76 percent / dimethylformamide / 6 h / 130 °C

21
[ 2715-70-0 ]
9-butyl-8-(7-methoxybenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 80 percent / dimethylformamide / 6 h / 130 °C

22
[ 2715-70-0 ]
8-(7-bromothiazolo[5,4-b]pyridin-2-ylsulfanyl)-9-butyl-9H-purine-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 81 percent / dimethylformamide / 6 h / 130 °C

23
[ 2715-70-0 ]
9-butyl-8-(6,7-dichlorobenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 81 percent / dimethylformamide / 6 h / 130 °C

24
[ 2715-70-0 ]
9-butyl-8-(7-ethoxybenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br₂; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 78 percent / dimethylformamide / 6 h / 130 °C

25
[ 2715-70-0 ]
1-(9-Butyl-9H-purin-6-ylamino)-2-methyl-1-phenyl-propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) t-BuOCl; 2.) aq. NaOH / methanol 2: (DHQ)2PHAL, K₂OsO₂(OH)4 / methanol; propan-1-ol / 50 °C

Reference： [1]Dress, K. Ruprecht; Goossen, Lukas J.; Liu, Hong; Jerina, Donald M.; Sharpless, K. Barry [Tetrahedron Letters, 1998, vol. 39, # 42, p. 7669 - 7672]

26
[ 2715-70-0 ]
(1S,2R)-1-(9-Butyl-9H-purin-6-ylamino)-1,2,3,4-tetrahydro-naphthalen-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) t-BuOCl; 2.) aq. NaOH / methanol 2: (DHQ)2PHAL, K₂OsO₂(OH)4 / methanol; propan-1-ol / 50 °C

Reference： [1]Dress, K. Ruprecht; Goossen, Lukas J.; Liu, Hong; Jerina, Donald M.; Sharpless, K. Barry [Tetrahedron Letters, 1998, vol. 39, # 42, p. 7669 - 7672]

27
[ 2715-70-0 ]
(1R,2R)-2-(9-Butyl-9H-purin-6-ylamino)-1,2-diphenyl-ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) t-BuOCl; 2.) aq. NaOH / methanol 2: (DHQ)2PHAL, K₂OsO₂(OH)4 / methanol; propan-1-ol / 50 °C

Reference： [1]Dress, K. Ruprecht; Goossen, Lukas J.; Liu, Hong; Jerina, Donald M.; Sharpless, K. Barry [Tetrahedron Letters, 1998, vol. 39, # 42, p. 7669 - 7672]

28
[ 542-69-8 ]
[ 134461-75-9 ]
[ 2715-70-0 ]

Yield	Reaction Conditions	Operation in experiment
51%	With caesium carbonate In N,N-dimethyl-formamide at 50℃;
51%	With caesium carbonate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Klein, Suzane M.; Zhang, Cungen; Jiang, Yu Lin [Tetrahedron Letters, 2008, vol. 49, # 16, p. 2638 - 2641]
[2]Location in patent: experimental part Lamale, Bassam; Henry, William P.; Daniels, Lee M.; Zhang, Cungen; Klein, Suzane M.; Jiang, Yu Lin [Tetrahedron, 2009, vol. 65, # 1, p. 62 - 69]

29
[ 2715-70-0 ]
[ 86-84-0 ]
[ 1093101-38-2 ]

Yield	Reaction Conditions	Operation in experiment
45%	In tetrahydrofuran Reflux;

Reference： [1]Location in patent: scheme or table Ghosh, Kumaresh; Sen, Tanushree [Tetrahedron Letters, 2008, vol. 49, # 50, p. 7204 - 7208]

30
[ 2715-70-0 ]
3-chloro-β-nitrostyrene [ No CAS ]
[ 1547236-52-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h;