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(2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide

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(2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide Basic information

Product Name:
(2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide
Synonyms:
  • 2,5-dichloro-N-(2-(diMethylphosphoryl)phenyl)pyriMidin-4-aMine
  • (2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide
  • 4-(orthodimethylphosphinylanilino)-5-chloro-2-chloropyrimidine
  • 2-[(2,5-Dichloro-4-pyrimidinyl)amino]phenyl]dimethylphosphine Oxide
  • 2,5-Dichloro-N-[2-(dimethylphosphinyl)phenyl]-4-pyrimidinamine
  • 4-Pyrimidinamine, 2,5-dichloro-N-[2-(dimethylphosphinyl)phenyl]-
  • 2,5-dichloro-N-(2-(dimethylphosphoryl)phenyl)pyrimidin-4-ami...
  • 2,5- Dichloro -N-[2- (dimethylphosphino) phenyl ]-4- pyrimidinamine *
CAS:
1197953-49-3
MF:
C12H12Cl2N3OP
MW:
316.12
EINECS:
1592732-453-0
Product Categories:
  • 1197953-49-3
Mol File:
1197953-49-3.mol
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(2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide Chemical Properties

Boiling point:
527.5±50.0 °C(Predicted)
Density 
1.41±0.1 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
pka
0.30±0.10(Predicted)
InChI
InChI=1S/C12H12Cl2N3OP/c1-19(2,18)10-6-4-3-5-9(10)16-11-8(13)7-15-12(14)17-11/h3-7H,1-2H3,(H,15,16,17)
InChIKey
XIKUAKVCJMVXCI-UHFFFAOYSA-N
SMILES
C1(Cl)=NC=C(Cl)C(NC2=CC=CC=C2P(C)(C)=O)=N1
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(2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide Usage And Synthesis

Description

(2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide is a pharmaceutical intermediate compound used in the synthesis of the antitumour agent Brigatinib. Brigatinib is an orally administered, potent, selective anaplastic lymphoma kinase ( Brigatinib is an oral, potent, selective anaplastic lymphoma kinase (ALK) and c-ros oncogene 1 (ROS1) tyrosine kinase inhibitor approved for the treatment of adult patients with advanced ALK-positive non-small cell lung cancer (NSCLC) who have not received prior ALK inhibitor therapy.

Uses

(2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide is an intermediate of AP26113 which is a kind of effective ALK inhibitor.

Synthesis

25 mL of a one-necked flask was added DMF (3 mL), 2,5,6-trichloro pyrimidine (0.72 g, 3.9 mmol) was added successively with stirring,2- (dimethylphosphonino) aniline (0.5 g, 3 mmol)Anhydrous potassium carbonate (0.62 g, 4.5 mmol), heated to 60 ° C and stirred for 4 h.(30 mL x 2), the organic phase was combined, washed with water (60 mL x 2), and the organic layer was dried over anhydrous sodium sulfate, and the organic layer was washed with ethyl acetate (30 mL) and water (30 mL) Filtered and concentrated, and the residue was passed through a silica gel column to give 0.8 g of a pale yellow solid (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide.

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