ChemicalBook > CAS DataBase List > 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine

5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine

Product Name
5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine
CAS No.
1337962-47-6
Chemical Name
5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine
Synonyms
EOS-62029;Taminadenant;Taminadenant (NIR178;PBF-509,Taminadenant;Taminadenant, 10 mM in DMSO;5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine;4-Pyrimidinamine, 5-bromo-2,6-di-1H-pyrazol-1-yl-;5-bromo-2,6-bis(1H-pyrazol-1-yl)pyrimidin-4-amine;5-bromo-2,6-di-(1H-pyrazol-1-yl)pyrimidine-4-amine;PBF509,PBF-509,P1 receptor,antitumor,tremor,Taminadenant,hemiparkinsonism,NIR-178,including catalepsy,PBF 509,Adenosine Receptor,inhibit,NIR 178,NIR178,Inhibitor,movement disorders
CBNumber
CB53142818
Molecular Formula
C10H8BrN7
Formula Weight
306.12
MOL File
1337962-47-6.mol
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5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine Property

Boiling point:
574.9±60.0 °C(Predicted)
Density 
1.93±0.1 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
DMSO : 125 mg/mL (408.34 mM; Need ultrasonic)
form 
Solid
pka
-0.39±0.10(Predicted)
color 
White to off-white
InChI
InChI=1S/C10H8BrN7/c11-7-8(12)15-10(18-6-2-4-14-18)16-9(7)17-5-1-3-13-17/h1-6H,(H2,12,15,16)
InChIKey
ATFXVNUWQOXRRU-UHFFFAOYSA-N
SMILES
BrC1=C(N=C(N2N=CC=C2)N=C1N1N=CC=C1)N
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

ChemScene
Product number
CS-0086930
Product name
Taminadenant
Purity
99.43%
Packaging
5mg
Price
$60
Updated
2021/12/16
ChemScene
Product number
CS-0086930
Product name
Taminadenant
Purity
99.43%
Packaging
10mg
Price
$100
Updated
2021/12/16
ChemScene
Product number
CS-0086930
Product name
Taminadenant
Purity
99.43%
Packaging
50mg
Price
$220
Updated
2021/12/16
ChemScene
Product number
CS-0086930
Product name
Taminadenant
Purity
99.43%
Packaging
100mg
Price
$320
Updated
2021/12/16
Alichem
Product number
1337962476
Product name
5-Bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine
Packaging
100mg
Price
$413
Updated
2021/12/16
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5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine Chemical Properties,Usage,Production

Uses

Taminadenant (NIR178; PBF509) is a highly potent and orally active adenosine A2A receptor (A2AR) antagonist. Taminadenant can antagonize A2AR agonist-mediated cAMP accumulation and impedance responses with KB values of 72.8 nM and 8.2 nM, respectively. Taminadenant reverses motor impairments in several rat models of movement disorders, including catalepsy, tremor, and hemiparkinsonism. Taminadenant can also inhibit tumor growth when combined with Spartalizumab.html" class="link-product" target="_blank">Spartalizumab (HY-P9972). Taminadenant reactivate the antitumor immune response[1][2].

Synthesis

288-13-1

1337962-43-2

1337962-47-6

General procedure for the synthesis of 5-bromo-2,6-bis(1H-pyrazol-1-yl)pyrimidin-4-amine from pyrazole and 5-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine: to a 3 mL DMF solution containing 0.15 g (0.55 mmol) of 5-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine (Intermediate 5). 0.11 g (1.64 mmol) of 1H-pyrazole and 0.18 g (0.55 mmol) of cesium carbonate were added sequentially. The reaction mixture was stirred at 85°C for 24 hours. After completion of the reaction, the solvent DMF was removed by distillation under reduced pressure. the crude product was washed with water and dried to give 0.13 g (77% yield) of the target compound.1H NMR (300 MHz, DMSO-d6) δ: 6.57 (dd, 1H), 6.60 (dd, 1H), 7.52 (s, 1H), 7.81 (d, 1H), 7.87 (d, 1H) , 8.41 (s, 1H), 8.51 (d, 1H), 8.60 (d, 1H).

in vivo

Taminadenant (PBF509) (0.3, 3, 7.5, 10, or 30 mg/kg; p.o.; single dosage) attenuates the cataleptic effects of Haloperidol, attenuates pilocarpine-induced tremulous jaw movement, enhances the effects of L-DOPA, shows a robust antiparkinsonian activity and displays antidyskinetic efficacy[1].

Animal Model:Sprague-Dawley rats (240-250 g; induced catalepsy by s.c. with 1 mg/kg Haloperidol (HY-14538))[1]
Dosage:3, 10, or 30 mg/kg
Administration:p.o.; single dosage
Result:Dose-dependently attenuated the cataleptic effects of Haloperidol when administered 1 h after Haloperidol injection.
Animal Model:Sprague-Dawley rats (240-250 g; induced tremulous jaw movement by s.c. with 1 mg/kg Pilocarpine (HY-B0726A))[1]
Dosage:0.3, 3, or 7.5 mg/kg
Administration:p.o.; single dosage
Result:Dose-dependently attenuated pilocarpine-induced tremulous jaw movement, being effective at the lowest dose tested.
Animal Model:Sprague-Dawley rats (240-250 g; induced hemiparkinsonian by unilateral injection of 6-OHDA (HY-B1081) in the medial forebrain bundle)[1]
Dosage:0.3 and 3 mg/kg
Administration:p.o.; single dosage
Result:Enhanced the effects of L-DOPA with a minimum efficacious dose (MED) of 3 mg/kg p.o..
Animal Model:Sprague-Dawley rats (240-250 g; induced dyskinesias by i.p. 4 mg/kg L-DOPA (HY-N0304) for 14 days and i.p. 15 mg/kg Benserazide hydrochloride (HY-B0404A))[1]
Dosage:0.3 or 3 mg/kg
Administration:p.o.; single dosage
Result:Showed a robust antiparkinsonian activity and displayed antidyskinetic efficacy.

References

[1] Nú?ez F, et al. PBF509, an Adenosine A2A Receptor Antagonist With Efficacy in Rodent Models of Movement Disorders. Front Pharmacol. 2018 Oct 19;9:1200. DOI:10.3389/fphar.2018.01200
[2] Chiappori AA, et al. Phase I Study of Taminadenant (PBF509/NIR178), an Adenosine 2A Receptor Antagonist, with or without Spartalizumab (PDR001), in Patients with Advanced Non-Small Cell Lung Cancer. Clin Cancer Res. 2022 Jun 1;28(11):2313-2320. DOI:10.1158/1078-0432.CCR-21-2742

5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine Preparation Products And Raw materials

Raw materials

Preparation Products

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5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine Suppliers

China 46 India 1 United States 2 Global 49
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1337962-47-6, 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amineRelated Search:


  • 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine
  • 5-bromo-2,6-di-(1H-pyrazol-1-yl)pyrimidine-4-amine
  • EOS-62029
  • Taminadenant
  • PBF-509,Taminadenant
  • 4-Pyrimidinamine, 5-bromo-2,6-di-1H-pyrazol-1-yl-
  • PBF509,PBF-509,P1 receptor,antitumor,tremor,Taminadenant,hemiparkinsonism,NIR-178,including catalepsy,PBF 509,Adenosine Receptor,inhibit,NIR 178,NIR178,Inhibitor,movement disorders
  • 5-bromo-2,6-bis(1H-pyrazol-1-yl)pyrimidin-4-amine
  • Taminadenant (NIR178
  • Taminadenant, 10 mM in DMSO
  • 1337962-47-6
  • C10H8BrN7