| Identification | Back Directory | [Name]
2,5-dichloro-N-(2-(diMethylphosphoryl)phenyl)pyriMidin-4-aMine | [CAS]
1197953-49-3 | [Synonyms]
2,5-dichloro-N-(2-(diMethylphosphoryl)phenyl)pyriMidin-4-aMine
4-(orthodimethylphosphinylanilino)-5-chloro-2-chloropyrimidine
2,5-Dichloro-N-[2-(dimethylphosphinyl)phenyl]-4-pyrimidinamine
4-Pyrimidinamine, 2,5-dichloro-N-[2-(dimethylphosphinyl)phenyl]-
2-[(2,5-Dichloro-4-pyrimidinyl)amino]phenyl]dimethylphosphine Oxide
(2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C12H12Cl2N3OP | [MDL Number]
MFCD29477700 | [MOL File]
1197953-49-3.mol | [Molecular Weight]
316.12 |
| Chemical Properties | Back Directory | [Boiling point ]
527.5±50.0 °C(Predicted) | [density ]
1.41±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
0.30±0.10(Predicted) | [Appearance]
Off-white to light yellow Solid | [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 |
| Hazard Information | Back Directory | [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.
| [References]
[1] Patent: CN106188138, 2016, A. Location in patent: Paragraph 0094-0096; 0106; 0107
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4948 - 4964
[3] Patent: EP3381925, 2018, A1. Location in patent: Paragraph 0158
[4] Patent: CN105330698, 2016, A. Location in patent: Paragraph 0196; 0197; 0198; 0199
[5] Patent: WO2012/151561, 2012, A1. Location in patent: Page/Page column 37-38 |
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