ChemicalBook CAS DataBase List 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile synthesis

6synthesis methods

Product Name:4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
CAS Number:24391-41-1
Molecular formula:C7H3ClN4
Molecular Weight:178.58

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime

908287-23-0

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

24391-41-1

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (865 mg, 4.40 mmol, 1.0 eq.) in dichloromethane (20 mL) was slowly added thionyl chloride (3.1 mL, 43.7 mmol, 10.0 eq.). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent. The residue was suspended in water (60 mL) and the pH was adjusted slowly to 4 by addition of saturated aqueous sodium bicarbonate.The precipitated solid was collected by diafiltration and washed sequentially with water and ethyl acetate to give the first products. Subsequently, the filtrate was extracted with ethyl acetate (50 mL x 3). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was combined with the aforementioned solid. The crude product was recrystallized in a mixed solvent of ethyl acetate/hexane (1:1, v/v) and dried under reduced pressure to give 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (763 mg, 97% yield).ESI-MS m/z: 178.8 [M + H]+, 176.8 [M - H]+.

908287-23-0
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24391-41-1
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Yield: 97%

Reaction Conditions:

with thionyl chloride in dichloromethane at 20;

Steps:

160 Example 160
To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (865 mg, 4.40 mmol, 1.0 eq) in DCM (20 mL), thionyl chloride (3.1 mL, 43.7 mmol, 10.0 eq) was added and the resulting mixture was stirred at RT overnight. The reaction mixture was concentrated in vacuo. The residue was suspended in water (60 mL) and saturated aqueous NaHC0₃ was added to adjust the pH to 4. The solid was collected by filtration, rinsed with water followed by ethyl acetate to afford the first batch of product. The filtrate was then extracted with ethyl acetate (50 mL x 3). The combined organic layer was washed with brine, dried over Na₂S0₄ and filtered. The filtrate was concentrated in vacuo and the residue was combined with the above -obtained solid. The crude product was then re -crystallized in ethyl acetate/hexanes (1 : 1) and dried in vacuo to afford 4-chloro-7H-pyrrolo[2,3- d]pyrimidine-5-carbonitrile (763 mg, 97% yield). ESI-MS m/z: 178.8 [M+H]⁺, 176.8 [M-H]

References:

INFINITY PHARMACEUTICALS INC.;INTELLIKINE, LLC;CASTRO, Alfredo, C.;EVANS, Catherine, A.;JANARDANANNAIR, Somarajannair;LESCARBEAU, Andre;LIU, Tao;SNYDER, Daniel, A.;TREMBLAY, Martin, R.;REN, Pingda;LIU, Yi;LI, Liansheng;CHAN, Katrina WO2013/12915, 2013, A1 Location in patent:Paragraph 00942

22276-95-5 Synthesis