2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical Properties

Density 

1.40±0.1 g/cm3(Predicted)

vapor pressure 

0-0Pa at 20-25℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Solid:particulate/powder

pka

2.78±0.30(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C14H17ClN4O/c1-18(2)13(20)11-7-9-8-16-14(15)17-12(9)19(11)10-5-3-4-6-10/h7-8,10H,3-6H2,1-2H3

InChIKey

PMDDQOHZLBZUSO-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C2C=C(C(N(C)C)=O)N(C3CCCC3)C2=N1

LogP

2.4 at 20℃ and pH7

CAS DataBase Reference

1211443-61-6

2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide Usage And Synthesis

Synthesis

To a three-necked flask was added 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-D]pyrimidine-6-carboxylic acid (26.57 g, 100 mmol) and N,N-dimethylformamide (133 mL), and the mixture was cooled to 0-5 °C under stirring. EDCI (23.00 g, 120 mmol) and a tetrahydrofuran solution of dimethylamine (2.0 M, 75 mL, 150 mmol) were then added. Triethylamine (20.24 g, 200 mmol) was added dropwise and the mixture was stirred at 20-25 °C for 6-8 hours. After completion of the reaction, the reaction mixture was extracted three times with ethyl acetate (133 mL) and the organic phases were combined. The organic phase was sequentially washed twice with water and once with brine (133 mL), dried with anhydrous sodium sulfate and concentrated. Finally, the target product 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (26.93 g, 92% yield) was purified by column chromatography in a mixed solvent of dichloromethane and methanol.

References

[1] Patent: CN106478641, 2017, A. Location in patent: Paragraph 0050; 0051; 0052
[2] Patent: WO2010/20675, 2010, A1. Location in patent: Page/Page column 89; 91

2-Chloro-7-cyclopentyl-N,N-dimethyl-H-pyrrolo[2,3-d]pyrimidine-6-carboxamide(1211443-61-6)Related Product Information

• 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyriMidine-6-carboxylic acid
• 4-Chloro-5,6-diMethyl-7H-pyrrolo[2,3-d]pyriMidine
• 7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol
• tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate
• (2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyriMidin-6-yl)Methanol
• 1-Piperazinecarboxylic acid, 4-[6-[[7-cyclopentyl-6-[(diMethylaMino)carbonyl]-7H-pyrrolo[2,3-d]pyriMidin-2-yl]aMino]-3-pyridinyl]-, 1,1-diMethylethyl ester
• LEE011 (succinate)