[ CAS No. 55405-67-9 ] {[proInfo.proName]}

Name: 55405-67-9|3-Bromopyrazolo[1,5-a]pyrimidine|97%
Brand: Ambeed
SKU: A138968
Price: 8.0 USD
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Quality Control of [ 55405-67-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55405-67-9 ]

SDS Specification

Alternatived Products of [ 55405-67-9 ]

Product Details of [ 55405-67-9 ]

CAS No. :	55405-67-9	MDL No. :	MFCD09832893
Formula :	C₆H₄BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MFJWRPLBWPDHGV-UHFFFAOYSA-N
M.W :	198.02	Pubchem ID :	12203208
Synonyms :

Calculated chemistry of [ 55405-67-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.69
TPSA :	30.19 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) :	-6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	1.02
Log Po/w (WLOGP) :	1.49
Log Po/w (MLOGP) :	1.35
Log Po/w (SILICOS-IT) :	1.2
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.38
Solubility :	0.833 mg/ml ; 0.0042 mol/l
Class :	Soluble
Log S (Ali) :	-1.24
Solubility :	11.3 mg/ml ; 0.0571 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.57
Solubility :	0.533 mg/ml ; 0.00269 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 55405-67-9 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310+P330-P302+P352-P305+P351+P338	UN#:	2811
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 55405-67-9 ]

* 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 [ 55405-67-9 ]
Downstream synthetic route of [ 55405-67-9 ]

[ 55405-67-9 ] Synthesis Path-Upstream 1~2

1
[ 274-71-5 ]
[ 55405-67-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With N-Bromosuccinimide In acetonitrile at 20℃; for 8 h;	To a solution of pyrazolo[1,5-ajpyrimidine (1 g, 8.39 mmol) in acetonitrile (5 mL) was added NBS (1.494 g, 8.39 mmol) and the reaction mixture stirred at room temperature for 8 h. The reaction mixture was concentrated under reduced pressure and the residue purified by silica gel chromatography (0-30percent petroleum ether/EtOAc) to afford 3-bromopyrazolo[1,5-ajpyrimidine (1.2 g, 6.06 mmol, 72percent yield) as a brown solid. LCMS (ESI) m/e 198.0 [(M+H), calcd for C6H5BrN3198.01; LC/MS retention time (method A2): tR = 1.43 mm.

Reference： [1] Patent: WO2017/59080, 2017, A1, . Location in patent: Page/Page column 256; 257

2
[ 16461-94-2 ]
[ 102-52-3 ]
[ 55405-67-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	for 4 h; Reflux	A. A solution of 3-amino-4-bromopyrazole (2.0 g, 12 mmol) and 1 ,1 ,3,3- tetramethoxypropane (4.1 mL, 25 mmol) in acetic acid (5 mL) was heated at reflux for 4 h. Water (2 mL) was added and the mixture heated at reflux for a further 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was triturated in methanol. The solid thus obtained was washed with cold methanol, ethyl acetate, and hexanes to provide 3-bromopyrazolo[1 ,5-a]pyrimidine as a brownish solid in 39percent yield (0.953 g): ¹H NMR (300 MHz, DMSO-d₆) £9.13 (d, J = 6.5 Hz, 1 H), 8.61 (s, 1 H), 8.35 (s, 1 H), 7.19-7.02 (m, 1 H); MS (ES+) m/z 197.9 (M + 1), 199.9 (M + 1).

Reference： [1] Patent: WO2013/64984, 2013, A1, . Location in patent: Page/Page column 66
[2] Patent: WO2009/85913, 2009, A1, . Location in patent: Page/Page column 68; 69

[ 55405-67-9 ] Synthesis Path-Downstream 1~22

2
[ 700871-79-0 ]
[ 55405-67-9 ]
[ 705263-72-5 ]

Yield	Reaction Conditions	Operation in experiment
4.5%	With potassium carbonate; triphenylphosphine;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; for 6h;Heating / reflux;	Weigh into a round bottom flask 3-bromopyrazolo [1, 5-a] pyrimidine (Lynch et al. Can. J. Chem. 1975, 53, 119-122; 0.095 g, 0.48 mmol), 2- (pyridin-2-yl)-5, 6-dihydro- 4H-pyrrolo [1, 2-b] pyrazole-3-boronic acid (Preparation 5; 0.10 g, 0.44 MMOL), triphenylphosphine (Aldrich; 0.007 g, 0.027 mmol) and tris (dibenzylideneacetone) dipalladium (0) (Aldrich; 0.015 g, 0.016 mmol). Add p-dioxane (6 ml) and 2. 0M aqueous potassium carbonate (2 mL). Stir and reflux under nitrogen for 6 h. Dilute with ethyl acetate, separate the organic layer, concentrate under reduced pressure, and chromatograph on flash silica using neat acetonitrile. Purify on a preparative reverse phase C-18 high-performance chromatography column using a gradient from 5% to 100% acetonitrile in 0.03% aqueous hydrochloric acid. Concentrate the pure fractions under reduced pressure, dissolve the residue in distilled water, and make basic by adding 1. OM aqueous sodium hydroxide. Extract with dichloromethane, dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 6 mg (4.5%) of the title compound as a yellow solid. TOF MS ES+ exact mass calculated for C17HL5N6 (MA : m/z = 303.1358 ; Found: 303. 1371.'H NMR (400 MHz, CDCL3) 8 8.66 (d, J = 2 Hz, 1H), 8. 64 (d, J = 2 Hz, 1H), 8.41 (dd, J = 4,2 Hz, 1H), 8.31 (s, 1H), 7.70 (M, 2H), 7.21 (M, 1H), 6.79 (dd, J = 7,4 Hz, 1H), 4.30 (t, J = 7 Hz, 2H), 3.10 (t, J = 8 Hz, 2H), 2.68 (M, 2H).

Reference： [1]Patent: WO2004/50659,2004,A1 .Location in patent: Page 103

3
[ 16461-94-2 ]
[ 102-52-3 ]
[ 55405-67-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	With acetic acid; for 4h;Reflux;	A. A solution of 3-amino-4-bromopyrazole (2.0 g, 12 mmol) and 1 ,1 ,3,3- tetramethoxypropane (4.1 mL, 25 mmol) in acetic acid (5 mL) was heated at reflux for 4 h. Water (2 mL) was added and the mixture heated at reflux for a further 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was triturated in methanol. The solid thus obtained was washed with cold methanol, ethyl acetate, and hexanes to provide 3-bromopyrazolo[1 ,5-a]pyrimidine as a brownish solid in 39% yield (0.953 g): 1H NMR (300 MHz, DMSO-d6) £9.13 (d, J = 6.5 Hz, 1 H), 8.61 (s, 1 H), 8.35 (s, 1 H), 7.19-7.02 (m, 1 H); MS (ES+) m/z 197.9 (M + 1), 199.9 (M + 1).
	With hydrogenchloride; In ethanol; water; at 20 - 71℃;	A solution of the amino-bromo-pyrazole obtained above, dissolved in EtOH (23OmL) was treated with cone. HCl (13.6mL) followed by tetra-methoxypropane (3 ImL) at rt. The resulting turbid solution was heated to 71C for 2h, during this time, the reaction mixture turned into a suspension and a solid started separating out. The reaction mixture was cooled to rt, the precipitated solid was collected by filtration, washed with EtOH (min vol.) and dried to obtain the desired compound. The crude compound (C) was used as such for the next step without further purification (26.8 g, 74.1%). (M + H): 198.0.

Reference： [1]Patent: WO2013/64984,2013,A1 .Location in patent: Page/Page column 66
[2]Patent: WO2009/85913,2009,A1 .Location in patent: Page/Page column 68; 69

4
[ 55405-67-9 ]
[ 73183-34-3 ]
[ 1169690-88-3 ]

Yield	Reaction Conditions	Operation in experiment
51.4%	With potassium acetate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 20 - 100℃;	To a stirred solution of compound 13f (27.8 mmol) in 1,4-dioxane (120 mL) was added B2Pm2 (126 mmol) and KOAc (101 mmol) at rt. The resulting mixture was purged with Ar for 45min, PdCl2(PPli3)2 (1.5 mmol) was added and the mixture again purged with Ar for 30min. The resulting mixture was heated to 1000C for 15h. The reaction <n="71"/>mixture was concentrated to obtain a viscous mass, which was charged over afluorosil plug, washed with pentane, followed by 60% EtOAc/Pet ether. The relevant fractions were concentrated to obtain a crude compound 13g as a pale yellow solid. The crude compound 13g was stirred with pentane (25mL) at -400C for 30min, filtered, washed with cold pentane (5mL) and dried under vacuum to obtain sufficiently pure compound (3.5g, 51.4%). TLC system: Ethyl acetate: Petroleum ether (2:3) Rf value: 0.4. (M + H): 246.3.
	With potassium acetate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; Sealed vessel;	PREPARATION 107 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine [Show Image] A mixture of <strong>[55405-67-9]3-bromopyrazolo[1,5-a]pyrimidine</strong> (1.00 g, 5.1 mmol), potassium acetate (1.78 g, 18.1 mmol) and bis(pinacolato)diboron (5.77 g, 22.7 mmol) in 1,4-dioxane (20 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and bis(triphenylphosphine)palladium(II) dichloride (0.180 g, 0.26 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was stirred with n-pentane (15 mL) at -40 C for 30 minutes. The solid was filtered, washed with cold pentane and dried in vacuo to give the title compound (1.66 g, >100%) as a solid which was used without further purification. LRMS (m/z): 246 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.26 (s, 12H), 6.89 (dd, 1H), 8.44 (s, 1H), 8.63 - 8.83 (m, 2H).
	With potassium acetate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; Sealed vessel;	PREPARATION 107 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine A mixture of <strong>[55405-67-9]3-bromopyrazolo[1,5-a]pyrimidine</strong> (1.00 g, 5.1 mmol), potassium acetate (1.78 g, 18.1 mmol) and bis(pinacolato)diboron (5.77 g, 22.7 mmol) in 1,4-dioxane (20 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and bis(triphenylphosphine)palladium(II) dichloride (0.180 g, 0.26 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was stirred with n-pentane (15 mL) at -40 C for 30 minutes. The solid was filtered, washed with cold pentane and dried in vacuo to give the title compound (1.66 g, >100%) as a solid which was used without further purification. LRMS (m/z): 246 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.26 (s, 12H), 6.89 (dd, 1H), 8.44 (s, 1H), 8.63 - 8.83 (m, 2H).

Reference： [1]Patent: WO2009/85913,2009,A1 .Location in patent: Page/Page column 68; 69-70
[2]Patent: EP2397482,2011,A1 .Location in patent: Page/Page column 109-110
[3]Patent: WO2011/157397,2011,A1 .Location in patent: Page/Page column 177

5
[ 55405-67-9 ]
[ 1066-54-2 ]
C₁₁H₁₃N₃Si [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10033 - 10046

6
[ 55405-67-9 ]
[ 1408000-31-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10033 - 10046

7
[ 55405-67-9 ]
[ 1407999-85-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10033 - 10046

8
[ 1527475-73-5 ]
[ 55405-67-9 ]
C₂₂H₂₉N₇O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); cesium fluoride; In 1,4-dioxane; water; at 100℃; for 18h;Microwave irradiation;	General procedure: To a solution of 6-bromopyridine-2-carbonitrile (80 mg, 0.44 mmol) and 4-(morpholin-4-yl)-5-(4,4, 5, 5-tetramethyl- 1, 3,2-d ioxaborolan-2-yl )-7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (P2) (241 mg, 0.523 mmol) in1,4-dioxane (2.5 mL) and water (0.5 mL) was addedtetrakis(triphenylphosphine)palladium(0) (51 mg, 44 pmol) and sodium carbonate (140 mg, 1.32 mmol). The reaction mixture was heated at 120 C under microwave irradiation for 15 minutes, then diluted with water (30 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentratedin vacuo; purification via preparative thin layer chromatography (Eluent: 1:1 petroleum ether ethyl acetate) afforded the product as a brown oil. Yield: 110 mg, 0.252 mmol, 57%. 1H NMR (400 MHz, CDCl3) 8.52 (s, 1H), 7.84-7.93 (m, 2H), 7.74 (s, 1H), 7.59 (dd, J=7.0, 1.2 Hz, 1H), 5.66 (s, 2H), 3.56-3.65 (m, 6H), 3.34-3.40 (m, 4H), 0.93 (dd, J8.3, 8.0 Hz, 2H), -0.05 (s, 9H).

Reference： [1]Patent: WO2014/1973,2014,A1 .Location in patent: Page/Page column 55; 114

9
[ 4334-88-7 ]
[ 55405-67-9 ]
ethyl 4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzoate [ No CAS ]