2-[(6-Chloro-3,4-dihydro-3-Methyl-2,4-dioxo-1(2h)-pyriMidinyl)Methyl]benzonitrile Chemical Properties

Melting point:

162-164°C

Boiling point:

418.0±55.0 °C(Predicted)

Density 

1.44

storage temp. 

2-8°C

solubility 

DMSO (Soluble, Sonicated), Methanol (Slightly, Heated, Sonicated)

form 

Solid

pka

-3.65±0.40(Predicted)

color 

White to Off-White

InChI

InChI=1S/C13H10ClN3O2/c1-16-12(18)6-11(14)17(13(16)19)8-10-5-3-2-4-9(10)7-15/h2-6H,8H2,1H3

InChIKey

BVUJISIVAHYNLI-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=CC=C1CN1C(=O)N(C)C(=O)C=C1Cl

2-[(6-Chloro-3,4-dihydro-3-Methyl-2,4-dioxo-1(2h)-pyriMidinyl)Methyl]benzonitrile Usage And Synthesis

Chemical Properties

White Solid

Uses

Alogliptin (A575425) intermediate.

Synthesis

Under stirring conditions, 20.8 g of dichloromethane, 3.21 g of 6-chloro-3-methyluracil, 4.51 g of 2-cyanobenzyl bromide and 5.16 g of DIPEA were sequentially added to the reaction flask.The reaction system was warmed up to refluxing temperature (40-45 °C) and the progress of the reaction was monitored by HPLC until the complete disappearance of 3-methyl-6-chlorouracil. Upon completion of the reaction, the reaction system was cooled to 20-25 °C and the dichloromethane was removed by distillation under reduced pressure. Water was added to the residue, stirred for 1 hour and filtered. The filter cake was washed with water, followed by ethanol and stirred at 20-25 °C for 1 hour. After filtration again, the filter cake was washed with ethanol and dried under reduced pressure at 60-70 °C to afford 5.28 g of white crystalline solid, i.e., the target product 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (hereinafter referred to as the intermediate), in 95.8% yield.

References

[1] Organic Letters, 2018, vol. 20, # 2, p. 473 - 476
[2] Patent: CN107954978, 2018, A. Location in patent: Paragraph 0042; 0043; 0051
[3] Patent: CN103819450, 2016, B. Location in patent: Paragraph 0034; 0038; 0039
[4] Patent: CN105367546, 2016, A. Location in patent: Paragraph 0013
[5] Patent: CN107556249, 2018, A. Location in patent: Paragraph 027; 0028

2-[(6-Chloro-3,4-dihydro-3-Methyl-2,4-dioxo-1(2h)-pyriMidinyl)Methyl]benzonitrile(865758-96-9)Related Product Information

• Benzonitrile, 2-[(tetrahydro-3-Methyl-2,4,6-trioxo-1(2H)-pyriMidinyl)Methyl]-
• 2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE
• (S)-Alogliptin Benzoate Salt
• Alogliptin Related Compound 14
• 2-(AMinoMethyl)benzonitrile hydrochloride
• Alogliptin Related Compound 26
• Alogliptin benzoate impurity K
• Alogliptin benzoate
• Alogliptin Impurity 34
• Alogliptin Related Compound 32
• Alogliptin Impurity 35
• Alogliptin Related Compound 21
• Alogliptin Impurity B
• (R)-2-((6-(3-((3-(2-cyanobenzyl)-1-Methyl-2,6-dioxo-1,2,3,6-tetrahydropyriMidin-4-yl)aMino)piperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)benzonitrile
• Alogliptin Impurity 16
• Alogliptin Impurity 10
• Alogliptin Related Compound 31
• Alogliptin Related Compound 24