2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine
• CAS No.: 90213-66-4
• Molecular Formula: C6H3Cl2N3
• Molecular Weight: 188.016
• Hs Code.: 29335990
• European Community (EC) Number: 618-507-6
• UNII: A2NE6H5F6Q
• DSSTox Substance ID: DTXSID80556131
• Nikkaji Number: J2.613.867A
• Wikidata: Q72468132
• Mol file: 90213-66-4.mol

Synonyms:2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine;90213-66-4;2,4-dichloro-1H-pyrrolo[2,3-d]pyrimidine;2,6-Dichloro-7-deazapurine;2,4-DICHLORO-7H-PYRROLO2,3-DPYRIMIDINE;2,4-Dichloro-7H-pyrrolo (2,3-d)pyrimidine;MFCD08059278;Tofacitinib Impurity 08;2,4-dichloropyrrolo[2,3-d]pyrimidine;1H-Pyrrolo[2,3-d]pyrimidine, 2,4-dichloro-;2,4-dichloro-7h-pyrrolo[2,3-d] pyrimidine;A2NE6H5F6Q;SCHEMBL352433;7H-PYRROLO[2,3-D]PYRIMIDINE, 2,4-DICHLORO-;DTXSID80556131;GHXBPCSSQOKKGB-UHFFFAOYSA-N;BCP00152;CS-B0455;CL3495;AKOS005256964;AKOS015907660;AC-4446;GS-6918;PB30992;PS-5648;HY-40350;SY003887;7H-2,4-dichloro-pyrrolo[2,3-d]pyrimidine;AM20120301;D4284;2,4-di chloro-7H-pyrrolo[2,3-d]pyrimidine;EN300-109601;2,4-bis(chloranyl)-7H-pyrrolo[2,3-d]pyrimidine;2-TRIFLUOROMETHYL-OXAZOLO[4,5-B]PYRIDINE;A843469;A1-00635;Q-103528;2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, AldrichCPR;Z1741972597

Chemical Property of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 0.0185mmHg at 25°C
• Melting Point: 247-250 °C
• Refractive Index: 1.805
• Boiling Point: 312oC at 760 mmHg
• PKA: 9.18±0.20(Predicted)
• Flash Point: 142.5oC
• PSA: 41.57000
• Density: 1.675 g/cm³
• LogP: 2.26470
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in DMSO, ethyl acetate and methanol. Slightly soluble in water.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 186.9704025
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dichloro-7-deazapurine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36-36/37/38-22
• Safety Statements: 26-45-28-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=C1C(=NC(=N2)Cl)Cl
• Uses: It is used as a pharmaceutical intermediate.

Technology Process of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

There total 3 articles about 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.3%

pyrrolo<2,3-d>pyrimidin-2,4-dione (39929-79-8) → 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (90213-66-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; at 70 - 80 ℃;

DOI:10.1016/j.ejmech.2012.03.015

Reference yield: 49.0%

7-deazaxanthine (39929-79-8) → 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (90213-66-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; at 75 - 105 ℃; for 18h;

DOI:10.1016/j.tet.2014.05.033

Reference yield: 43.0%

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (90213-66-4)

Guidance literature:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine; With antimony(III) chloride; In 1,2-dichloro-ethane; at -10 ℃; for 0.0833333h;

With tert.-butylnitrite; In 1,2-dichloro-ethane; at -10 ℃; for 3h;

upstream raw materials:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

pyrrolo<2,3-d>pyrimidin-2,4-dione

7-deazaxanthine

Downstream raw materials:

2'-deoxy-7-deazaadenosine

2-amino-4-chloro-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-Amino-2-chlor-7-<2-desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo-<2,3-d>pyrimidin

(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-2-chloro-N-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine

Refernces

• 1、 -. "Preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride". Paragraph 0022-0024. . Retrieved 2020/04/17.
• 2、 -. "Fused-pyrimidine derivatives, preparation method thereof, and pharmaceutical composition for use in preventing or treating Bruton's tyrosine kinase activity related diseases containing the same as an active ingredient". Paragraph 0594; 0595; 0600-0602. . Retrieved 2019/02/02.