[ CAS No. 195044-14-5 ] {[proInfo.proName]}

Name: 195044-14-5|2-Bromo-6-tert-butylpyridine|95%
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Quality Control of [ 195044-14-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 195044-14-5 ]

Product Details of [ 195044-14-5 ]

CAS No. :	195044-14-5	MDL No. :	MFCD09607717
Formula :	C₉H₁₂BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QMVOIXCANJLTGO-UHFFFAOYSA-N
M.W :	214.10	Pubchem ID :	22113415
Synonyms :

Calculated chemistry of [ 195044-14-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.44
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.21
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.56
Log Po/w (XLOGP3) :	3.58
Log Po/w (WLOGP) :	3.14
Log Po/w (MLOGP) :	2.51
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	2.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.76
Solubility :	0.0372 mg/ml ; 0.000174 mol/l
Class :	Soluble
Log S (Ali) :	-3.54
Solubility :	0.0622 mg/ml ; 0.00029 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.09
Solubility :	0.0172 mg/ml ; 0.0000805 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.93

Safety of [ 195044-14-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 195044-14-5 ]

* 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 [ 195044-14-5 ]
Downstream synthetic route of [ 195044-14-5 ]

[ 195044-14-5 ] Synthesis Path-Upstream 1~4

1
[ 626-05-1 ]
[ 677-22-5 ]
[ 195044-14-5 ]

Yield	Reaction Conditions	Operation in experiment
10 g	With copper(l) iodide In tetrahydrofuran at 0 - 20℃; for 1 h; Inert atmosphere	3neckflask, to introduce a nitrogen atmosphere, 2,6dibromopyridine14.24g, iodine screen copper (I) 0.61g, tetrahydrofuran (dehydration solvent commerciallyavailable) 180mL, and cooled to 0 . Thereto, was added dropwise to 70mL 1.0M tetrahydrofuran solution of tbutylmagnesium chloride was stirred at roomtemperature for 1 hour. Saturated aqueous ammonium chloride solution 100mL, 100mL ethyl acetate and the resulting crude by concentration of the resultingorganic layer was extracted by liquid separation, by adding a product ( ) was purified by silica gel column chromatography (solvent: hexane) by purifyingthe 2bromo6tbutylpyridine to give 10g.

Reference： [1] Organometallics, 2018, vol. 37, # 7, p. 1123 - 1132
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 24, p. 6277 - 6282[3] Angew. Chem., 2013, vol. 125, # 24, p. 6397 - 6402,6
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 10, p. 4528 - 4560
[5] Patent: KR2015/128789, 2015, A, . Location in patent: Paragraph 0813; 0814

2
[ 626-05-1 ]
[ 195044-14-5 ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol	2,6-Dibromopyridine (50 g) was added to a solution of potassium tert-butoxide (35.5 g) in tert-butanol (300 ml). The mixture was heated to reflux for 3.5 hours then cooled and concentrated. The residue was quenched with water and extracted into ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated to give 2-bromo-6-tert-butylpyridine (21.4 g, 44percent yield) as a clear oil; ¹H NMR (270 MHz): δ 1.55(9H,s), 6.58(1H,d), 6.98(1H,d), 7.33(1H,t)ppm.

Reference： [1] Patent: US6169101, 2001, A,

3
[ 626-05-1 ]
[ 594-19-4 ]
[ 195044-14-5 ]

Reference： [1] New Journal of Chemistry, 2008, vol. 32, # 12, p. 2150 - 2158
[2] Chemistry - An Asian Journal, 2013, vol. 8, # 9, p. 2033 - 2045

4
[ 58498-57-0 ]
[ 195044-14-5 ]

Reference： [1] Journal of the American Chemical Society, 2004, vol. 126, # 39, p. 12232 - 12233

[ 195044-14-5 ] Synthesis Path-Downstream 1~88

1
[ 626-05-1 ]
[ 195044-14-5 ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium tert-butylate; In tert-butyl alcohol;	2,6-Dibromopyridine (50 g) was added to a solution of potassium tert-butoxide (35.5 g) in tert-butanol (300 ml). The mixture was heated to reflux for 3.5 hours then cooled and concentrated. The residue was quenched with water and extracted into ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated to give 2-bromo-6-tert-butylpyridine (21.4 g, 44% yield) as a clear oil; 1H NMR (270 MHz): delta 1.55(9H,s), 6.58(1H,d), 6.98(1H,d), 7.33(1H,t)ppm.

Reference： [1]Patent: US6169101,2001,A

2
[ 811-62-1 ]
[ 195044-14-5 ]
[ 290333-91-4 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 20 - 21

3
[ 626-05-1 ]
t-BuCuCNLi*LiCl [ No CAS ]
[ 195044-14-5 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 3471 - 3474

4
[ 97634-83-8 ]
[ 195044-14-5 ]
[ 1037223-45-2 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 3471 - 3474
[2]New Journal of Chemistry,2008,vol. 32,p. 2150 - 2158

5
[ 195044-14-5 ]
[ 97634-83-8 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 3471 - 3474
[2]New Journal of Chemistry,2008,vol. 32,p. 2150 - 2158

6
[ 626-05-1 ]
[ 594-19-4 ]
[ 195044-14-5 ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4249 - 4255
[2]New Journal of Chemistry,2008,vol. 32,p. 2150 - 2158
[3]Journal of the American Chemical Society,2020,vol. 142,p. 564 - 572
[4]Chemistry - An Asian Journal,2013,vol. 8,p. 2033 - 2045

7
[ 6831-86-3 ]
[ 195044-14-5 ]
[ 1105699-41-9 ]

Reference： [1]New Journal of Chemistry,2008,vol. 32,p. 2150 - 2158

8
[ 917-54-4 ]
[ 195044-14-5 ]
[ 6831-86-3 ]

Reference： [1]New Journal of Chemistry,2008,vol. 32,p. 2150 - 2158

9
[ 67-56-1 ]
[ 201230-82-2 ]
[ 195044-14-5 ]
[ 1211588-48-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine;1,3-bis-(diphenylphosphino)propane; palladium diacetate; at 70℃; under 30003.0 Torr; for 12h;	Preparative Example P1Step 1 : Methyl 6-(tert-butvhpicolinate (P1a)To the solution of <strong>[195044-14-5]2-bromo-6-(tert-butyl)pyridine</strong> (20.0 g, 93.9 mmol) in MeOH (100 mL) was added dppp (3.86 g, 9.39 mmol), Pd(OAc)2 (6.32 g, 9.39 mmol) and TauEpsilonXiAlpha (28.5 g, 281 mmol) and then the mixture was stirred under CO (4 MPa) at 70C for 12 h. The reaction mixture was filtered, concentrated and purified by CC (RhoEpsilonXi/EpsilonAlpha = 40/1) to give compound P1a (12.0 g, 66%) as a colorless oil.

Reference： [1]Patent: WO2012/139775,2012,A1 .Location in patent: Page/Page column 35

10
[ 195044-14-5 ]
[ 1392146-24-5 ]

Reference： [1]Patent: WO2012/139775,2012,A1

11
[ 79-44-7 ]
[ 195044-14-5 ]
[ 1309314-68-8 ]

Yield	Reaction Conditions	Operation in experiment
67%		A : Bis(6-tert-butylpyridin-2-yl)methanone 80 ml (200 mmol) of n-butyllithium (2.5 N) are added dropwise to a suspension, cooled to -78 C., of 45.0 g (210 mmol) of <strong>[195044-14-5]2-bromo-6-tert-butylpyridine</strong> [195044-14-5] in 500 ml of diethyl ether, and the mixture is stirred at -78 C. until a yellow solution forms. The yellow solution is stirred at -78 C. for a further 30 min., 9.2 ml (100 mmol) of N,N-dimethylcarbamoyl chloride [79-44-7] are then added, and the mixture is again stirred at -78 C. for a further 30 min. After warming to 0 C., a mixture of 100 ml of water and 2 ml of glacial acetic acid is added dropwise, the mixture is stirred for a further 30 min., and the precipitated solid is then filtered off with suction, washed once with 25 ml of diethyl ether and once with 25 ml of ethanol and dried in vacuo. Yield: 19.9 g (67 mmol), 67%, 97% pure according to 1H-NMR.

Reference： [1]Patent: US2012/286254,2012,A1 .Location in patent: Page/Page column 22

12
[ 195044-14-5 ]
[ 1309314-69-9 ]

Reference： [1]Patent: US2012/286254,2012,A1

13
[ 195044-14-5 ]
[ 1309314-70-2 ]

Reference： [1]Patent: US2012/286254,2012,A1

14
[ 195044-14-5 ]
[ 1309314-71-3 ]

Reference： [1]Patent: US2012/286254,2012,A1

15
[ 195044-14-5 ]
[ 1309314-74-6 ]

Reference： [1]Patent: US2012/286254,2012,A1

16
[ 195044-14-5 ]
[ 1309314-73-5 ]

Reference： [1]Patent: US2012/286254,2012,A1

17
[ 195044-14-5 ]
[ 1309314-49-5 ]

Reference： [1]Patent: US2012/286254,2012,A1

18
[ 195044-14-5 ]
[ 1309314-72-4 ]

Reference： [1]Patent: US2012/286254,2012,A1

19
[ 195044-14-5 ]
[ 1309314-50-8 ]

Reference： [1]Patent: US2012/286254,2012,A1

20
[ 100-53-8 ]
[ 195044-14-5 ]
[ 1429200-00-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 50℃; for 16h;	Example 58A[0972] 2-(benzylthio)-6-tert-butylpyridine[0973] To a solution of benzyl mercaptan (0.22 mL, 1.87 mmol) in anhydrous N,N- dimethylformamide (10 mL) was added a 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (1.87 mL, 1.87 mmol) dropwise over 2 minutes. To the resulting suspension was added <strong>[195044-14-5]2-bromo-6-tert-butylpyridine</strong> (0.20 g, 0.93 mmol), and the resulting mixture was stirred at 50 C for 16 hours. The cooled mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL), and the ethyl acetate layer was dried over Na2S04, filtered and concentrated in vacuo to give a crude product. Purification by column chromatography on silica gel using hexanes gave the titled compound. XH NMR (300 MHz, CDC13) delta ppm 1.35 (s, 9 H), 4.50 (s, 2 H), 6.93 - 7.03 (m, 2 H), 7.17 - 7.45 (m, 6 H); MS (APCI) m/z 258.3 (M+H)+.

Reference： [1]Patent: WO2013/49174,2013,A1 .Location in patent: Paragraph 0972-0973

21
[ 626-05-1 ]
[ 677-22-5 ]
[ 195044-14-5 ]

Yield	Reaction Conditions	Operation in experiment
10 g	With copper(l) iodide; In tetrahydrofuran; at 0 - 20℃; for 1h;Inert atmosphere;	3neckflask, to introduce a nitrogen atmosphere, 2,6dibromopyridine14.24g, iodine screen copper (I) 0.61g, tetrahydrofuran (dehydration solvent commerciallyavailable) 180mL, and cooled to 0 . Thereto, was added dropwise to 70mL 1.0M tetrahydrofuran solution of tbutylmagnesium chloride was stirred at roomtemperature for 1 hour. Saturated aqueous ammonium chloride solution 100mL, 100mL ethyl acetate and the resulting crude by concentration of the resultingorganic layer was extracted by liquid separation, by adding a product ( ) was purified by silica gel column chromatography (solvent: hexane) by purifyingthe 2bromo6tbutylpyridine to give 10g.

Reference： [1]Organometallics,2018,vol. 37,p. 1123 - 1132
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 6277 - 6282
Angew. Chem.,2013,vol. 125,p. 6397 - 6402,6
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 4528 - 4560
[4]Patent: KR2015/128789,2015,A .Location in patent: Paragraph 0813; 0814

22
[ 195044-14-5 ]
2-(tert-butyl)-6-bromopyridine 1-oxide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6277 - 6282
Angew. Chem.,2013,vol. 125,p. 6397 - 6402,6

23
[ 127049-52-9 ]
[ 195044-14-5 ]
(S)-6-(1-hydroxy-2,2-dimethylpropyl)-6'-t-butyl-2,2'-bipyridine [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2013,vol. 8,p. 2033 - 2045

24
[ 10365-98-7 ]
[ 195044-14-5 ]
2-(tert-butyl)-6-(3-methoxyphenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; for 12h;Reflux; Inert atmosphere;	To a 250 mL three-necked flask was added 3-methoxyphenylboronic acid (3.1 g, 20.0 mmol) K2CO3 (5.8 g, 42.0 mmol), and then a reflux device was set up, and the gas was purged three times in an argon atmosphere. 2-Bromo-6-tert-butylpyridine (3.6 g, 16.8 mmol), solvent ethylene glycol dimethyl ether (30 mL) and distilled water (20 mL) were added. The system was then bubbled with a long needle for 30 min and then tetrakistriphenylphosphine palladium (1.0 g, 0.9 mmol) was added. The system was heated to reflux for 12 h under argon. After the reaction was completed, the system was cooled to room temperature, and ethyl acetate (30 mL EtOAc) was evaporated. 1:100), 2.7 g of colorless oil2-(3-Methoxyphenyl)-6-tert-butylpyridine, yield 67%.

Reference： [1]Chemical Communications,2014,vol. 50,p. 11056 - 11059
[2]Patent: CN104804041,2018,B .Location in patent: Paragraph 0043; 0171-173

25
[ 195044-14-5 ]
3-(6-(tert-butyl)pyridin-2-yl)phenol hydrobromide [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 11056 - 11059

26
[ 195044-14-5 ]
2-(tert-butyl)-6-(3-((di-tert-butylphosphino)oxy)phenyl)pyridine [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 11056 - 11059
[2]Patent: CN104804041,2018,B

27
[ 195044-14-5 ]
(<SUP>tBu</SUP>NC<SUP>O</SUP>P)IrHCl [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 11056 - 11059
[2]Patent: CN104804041,2018,B

28
[ 195044-14-5 ]
[6-(tert-butyl)pyridine-2-yl]methyl}lithium [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 9992 - 10002

29
[ 195044-14-5 ]
6-but-3′-enyl-2-tert-butylpyridine [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 9992 - 10002

30
[ 195044-14-5 ]
6-{4′-[bis(perfluorophenyl)boranyl]butyl}-2-tert-butylpyridine [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 9992 - 10002

31
[ 74-88-4 ]
[ 195044-14-5 ]
[ 6831-86-3 ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 564 - 572
[2]Dalton Transactions,2015,vol. 44,p. 9992 - 10002

32
[ 124-38-9 ]
[ 195044-14-5 ]
[ 848027-99-6 ]

Yield	Reaction Conditions	Operation in experiment
2 g		Next, the threeneckflask, to introduce a nitrogen atmosphere, the above synthesis of 2bromo6tbutylpyridine 3.65g, tetrahydrofuran (dehydration solventcommercially available) 50mL, and cooled to 78. Thereto, a 1.6M solution of nbutyllithiumin hexane was added dropwise 10.0mL, was stirred for 30 minutesat 78. Here, by the addition of crushed dry ice and slowly a large excess, and the mixture was stirred at room temperature for 2 hours. By extraction andseparated with the addition of 100mL of water, 50mL of ethyl acetate was recovered aqueous layer (pH ~ 11). With respect to the aqueous layer, concentratedhydrochloric acid to pH ~ 2 was added little by little and, by concentration of the resulting organic layer was extracted three times with 50mL of ethyl acetate, togive 2g Compound A214.

Reference： [1]Patent: KR2015/128789,2015,A .Location in patent: Paragraph 0811; 0813; 0815

33
[ 195044-14-5 ]
2-(3-(bromomethyl)phenyl)-6-(tert-butyl)pyridine hydrobromide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1614 - 1618
Angew. Chem.,2017,vol. 129,p. 1636 - 1640,5

34
[ 195044-14-5 ]
2-(tert-butyl)-6-(3-((di-tert-butylphosphino)methyl)phenyl)pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1614 - 1618
Angew. Chem.,2017,vol. 129,p. 1636 - 1640,5

35
[ 87199-15-3 ]
[ 195044-14-5 ]
(3-(6-(tert-butyl)pyridin-2-yl)phenyl)methanol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1614 - 1618
Angew. Chem.,2017,vol. 129,p. 1636 - 1640,5

36
[ 195044-14-5 ]
C₂₂H₃₀I₂N₄Rh⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 1123 - 1132

37
[ 195044-14-5 ]
C₂₄H₃₂I₂N₅Rh [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 1123 - 1132

38
[ 195044-14-5 ]
C₂₂H₃₁N₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 1123 - 1132

39
[ 195044-14-5 ]
C₂₂H₃₁N₄⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 1123 - 1132

40
[ 195044-14-5 ]
C₄₄H₆₀CuN₈⁽¹⁺⁾*0.5Cu₂I₄^(2-) [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 1123 - 1132

41
[ 109-76-2 ]
[ 195044-14-5 ]
N,N’‐bis‐[6‐tert‐butyl‐2-pyridyl]propane‐1,3‐diamine [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 1123 - 1132

42
[ 57260-71-6 ]
[ 195044-14-5 ]
4-tert-butoxycarbonyl-1-(6-tert-butylpyridin-2-yl)piperazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4528 - 4560

43
[ 195044-14-5 ]
Nε-acryloyl-L-lysine-4-(6-tert-butylpyridin-2-yl)piperazide*2TFA [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4528 - 4560

44
[ 195044-14-5 ]
C₂₄H₃₄F₃N₅O₃*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4528 - 4560

45
[ 195044-14-5 ]
[ 120145-34-8 ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4528 - 4560

46
[ 195044-14-5 ]
Nα-Boc-Nε-acryloyl-L-lysine-4-(6-tert-butylpyridin-2-yl)piperazide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4528 - 4560

47
[ 195044-14-5 ]
2-(3-methoxyphenyl)-6-t-butylpyridine hydrobromide [ No CAS ]

Reference： [1]Patent: CN104804041,2018,B

48
[ 5720-05-8 ]
[ 195044-14-5 ]
[ 140136-60-3 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 11104 - 11107

49
[ 195044-14-5 ]
tert-butyl 7-((1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

50
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-6-((1,2,3,4-tetrahydroisoquinolin-7-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one dihydrochloride [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

51
[ 195044-14-5 ]
tert-butyl 6-((1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

52
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-6-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one hydrochloride [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

53
[ 195044-14-5 ]
tert-butyl 6-((2-isopropyl-1-(6-(2-fluoropropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

54
[ 195044-14-5 ]
tert-butyl 6-((1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

55
[ 195044-14-5 ]
2-isopropyl-1-(6-(2-fluoropropan-2-yl)pyridin-2-yl)-6-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

56
[ 195044-14-5 ]
tert-butyl 6-((2-cyclopropyl-1-(6-(2-fluoropropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

57
[ 195044-14-5 ]
tert-butyl 6-((1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

58
[ 195044-14-5 ]
tert-butyl 7-((1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

59
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-((1,2,3,4-tetrahydroisoquinolin-7-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one dihydrochloride [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

60
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one dihydrochloride [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

61
[ 195044-14-5 ]
2-cyclopropyl-1-(6-(2-fluoropropan-2-yl)pyridin-2-yl)-6-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

62
[ 195044-14-5 ]
tert-butyl 7-((1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

63
[ 195044-14-5 ]
tert-butyl 7-(2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

64
[ 195044-14-5 ]
2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

65
[ 195044-14-5 ]
tert-butyl 7-(1-(6-tert-butylpyridin-2-yl)-3-oxo-2-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

66
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

67
[ 195044-14-5 ]
tert-butyl 7-(1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

68
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

69
[ 955368-93-1 ]
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.4%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 90℃;	Step-1: Synthesis of 1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (400 mg, 1.78 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-(tert-butyl)pyridine</strong> (458 mg, 2.14 mmol, 1.20 eq) in (12 mL) of dioxane was added potassium carbonate (492 mg, 3.56 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 10 min followed by addition of copper iodide (68 mg, 0.356 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (63 mg, 0.712 mmol, 0.4 eq) and again purged with nitrogen for 10 min, stirred at 90 C. for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-30% EtOAc in hexane] to afford the desired product, 1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (366 mg, 57.40%) as colorless liquid. LCMS: 358.2 [M+1]+

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0618; 0619; 0625-0627

70
2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.51%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 90℃;	Step-1: Synthesis of 1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (500 mg, 2.242 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-(tert-butyl)pyridine</strong> (586 mg, 2.690 mmol, 1.20 eq) in (12 mL) of dioxane was added potassium carbonate (619 mg, 4.484 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 10 min followed by addition of copper iodide (85 mg, 0.448 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (80 mg, 0.896 mmol, 0.4 eq) and again purged with nitrogen for 10 min, stirred at 90 C. for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-30% EtOAc in hexane] to afford the desired product, 1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (300 mg, 37.51%) as light yellow viscous.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0610-0612; 0643-0645

71
[ 626-05-1 ]
[ 2259-30-5 ]
[ 195044-14-5 ]

Yield	Reaction Conditions	Operation in experiment
87.19%	With copper(l) iodide; In tetrahydrofuran; at 0 - 20℃; for 1h;	Step-1: Synthesis of 2-bromo-6-(tert-butyl)pyridine To a stirred solution of 2,6-dibromopyridine (1.0 g, 4.221 mmol, 1.0 eq) in (30.0 mL) of THF was added CuI (40 mg, 0.211 mmol, 0.05 eq) followed by addition of 2.0M solution of tert-butylmagnesium bromide (8.44 mL, 16.885 mmol, 4.0 eq) at 0 C. The reaction mixture was stirred at RT for 1 h. The progress of reaction was monitored by LCMS. The reaction mixture was quenched with saturated solution of NH4Cl (50 mL), extracted with EtOAc (2*100 mL), the combined organic layers were washed with water (50 mL), dried over Na2SO4, concentrated to afford the desired compound 2-bromo-6-(tert-butyl)pyridine (790 mg, 87.19%) as Light yellow liquid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0475-0477

72
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one dihydrochloride [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

73
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-((1,2,3,4-tetrahydroisoquinolin-7-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one dihydrochloride [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

74
[ 195044-14-5 ]
tert-butyl 7-(1-(6-tert-butylpyridin-2-yl)-3-oxo-2-(1,1,1-trifluoropropan-2-yl)-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

75
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one hydrochloride [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

76
[ 195044-14-5 ]
tert-butyl 7-(1-(6-tert-butylpyridin-2-yl)-2-(2-methoxyethyl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

77
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-2-(2-methoxyethyl)-6-(1,2,3,4-tetrahydro isoquinolin-7-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Reference： [1]Patent: US2019/106427,2019,A1

78
6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.02%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 16h;	Step-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 0.359 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-tert-butylpyridine</strong> (92.33 mg, 0.431 mmol, 1.2 eq) in 1,4 dioxane (5 mL) was added potassium carbonate (99.2 mg, 0.718 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (13.67 mg, 0.0718 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (12.65 mg, 0.143 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 16 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product which was purified by flash chromatography (Teledyne Isco Rf+); to afford 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3 (2H)-one (100 mg, 68.02%) as off white solid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0667; 0676; 0677

79
2-tert-butyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]
[ 195044-14-5 ]
2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.71%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 5h;	Step-3: Synthesis of 2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-tert-butyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (180 mg, 0.756 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-tert-butylpyridine</strong> (194.3 mg, 0.907 mmol, 1.2 eq) in 1,4 dioxane (5 mL) was added potassium carbonate (208.9 mg, 1.512 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (28.7 mg, 0.151 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (26.05 mg, 0.302 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 30% EtOAc/Hexane to afford 2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 35.71%) as off white solid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0683; 0688; 0689

80
6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.15%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 5h;	Step-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (90 mg, 0.719 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-tert-butylpyridine</strong> (184.7 mg, 0.862 mmol, 1.2 eq) in 1,4 dioxane (3 mL) was added potassium carbonate (198.7 mg, 1.438 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (27.38 mg, 0.143 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (25.35 mg, 0.287 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resulting mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). The combined organic layers were washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 30% EtOAc/Hexane to afford pure 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (180 mg, 63.15%) as off white solid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0695; 0704; 0705

81
2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.25%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 5h;	Step-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (200 mg, 0.833 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-tert-butylpyridine</strong> (214 mg, 0.999 mmol, 1.2 eq) in 1,4 dioxane (3 mL) was added potassium carbonate (230 mg, 1.666 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (31 mg, 0.666 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (30 mg, 0.333 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 95% EtOAc/Hexane to afford 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 32.25%) as off white solid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0711; 0720; 0721

82
2-(2-methoxyethyl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]
[ 195044-14-5 ]
1-(6-tert-butylpyridin-2-yl)-2-(2-methoxyethyl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.91%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110℃; for 5h;	To a stirred solution of 2-(2-methoxyethyl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (300 mg, 1.248 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-tert-butylpyridine</strong> (320 mg, 1.497 mmol, 1.2 eq) in dioxane (6 mL) was added potassium carbonate (344.7 mg, 2.496 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (47.53 mg, 0.249 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (44 mg, 0.499 mmol, 0.4 eq) and again purged with nitrogen for 30 min. The resultant mixture was heated at 110 C. for 5 h. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 50% EtOAc/Hexane to afford pure to afford 1-(6-tert-butylpyridin-2-yl)-2-(2-methoxyethyl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3 (2H)-one (200 mg, 42.91%).

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0727; 0738; 0739

83
[ 955370-02-2 ]
[ 195044-14-5 ]
1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.77%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 90℃;	Step-2: Synthesis of 1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-ethyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (600 mg, 2.853 mmol, 1.0 eq) and <strong>[195044-14-5]2-bromo-6-(tert-butyl)pyridine</strong> (734 mg, 3.424 mmol, 1.20 eq) in (20 mL) of dioxane was added Potassium carbonate (788 mg, 5.706 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 10 min followed by addition of copper iodide (109 mg, 0.570 mmol, 0.2 eq), and N,N'-dimethylethylenediamine (DMEDA) (0.123 mL, 1.141 mmol, 0.4 eq) and again purged with nitrogen for 10 min, stirred at 90 C. for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-30% EtOAc in hexane] to afford the desired compound 1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (380 mg, 38.77%) as light yellow solid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 0475; 0478; 0479

84
[ 195044-14-5 ]
C₄₆H₆₈N₅P₂Rh₂ [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4249 - 4255

85
[ 195044-14-5 ]
6-(tert-butyl)-6′-[(di-tert-butylphosphino)methyl]-2,2′-bipyridine [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4249 - 4255

86
[ 195044-14-5 ]
C₂₄H₃₅N₂OPRh⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4249 - 4255

87
[ 195044-14-5 ]
C₂₃H₃₅ClN₂PRh [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4249 - 4255

88
[ 195044-14-5 ]
C₂₃H₃₅N₅PRh [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4249 - 4255

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 195044-14-5 ] {[proInfo.proName]}

Quality Control of [ 195044-14-5 ]

Related Doc. of [ 195044-14-5 ]

Product Details of [ 195044-14-5 ]

Calculated chemistry of [ 195044-14-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 195044-14-5 ]

Application In Synthesis of [ 195044-14-5 ]

[ 195044-14-5 ] Synthesis Path-Upstream 1~4

[ 195044-14-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 195044-14-5 ]

Bromides

Related Parent Nucleus of [ 195044-14-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 195044-14-5 ]

Related Parent Nucleus of
[ 195044-14-5 ]