4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine Chemical Properties

Boiling point:

284℃

Density 

1.76

Flash point:

125℃

storage temp. 

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

pka

-0.19±0.10(Predicted)

Appearance

Light yellow to light brown Solid

InChI

InChI=1S/C6H4Cl2N4/c1-12-5-3(2-9-12)4(7)10-6(8)11-5/h2H,1H3

InChIKey

TYMWHTJGWKSXRY-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=C2C=NN(C)C2=N1

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HS Code 

2933599590

4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine Usage And Synthesis

Synthesis

4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine is prepared by the reaction of Methylhydrazine and 2,4,6-trichloropyrimidine-5-carbaldehyde. The specific synthesis steps are as follows:
To a solution of 2,4,6-trichloropyrimidine-5-carbaldehyde (8 g, 37.84 mmol, 1.00 equiv) in ethanol (120 mL) was added a 40percent water solution of methylhydrazine (4 mL, 37.98 mmol, 1.00 equiv) and triethylamine (16 mL) at -78° C. The resulting mixture was stirred for 30 min at -78° C. and then 2 h at 0° C. After completion the reaction was concentrated under vacuum without heating. Then ethyl acetate was added and the solution was washed with saturated ammonium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum without heating. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:1) to afford 6 g (78percent) of 4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine as a white solid. LC-MS (ES, m/z): 203 [M+H]+.

References

[1] Patent: US2015/57260, 2015, A1. Location in patent: Paragraph 0414; 0415
[2] Patent: WO2015/25026, 2015, A1. Location in patent: Page/Page column 114
[3] Patent: WO2017/133664, 2017, A1. Location in patent: Page/Page column 83
[4] Patent: US2008/234262, 2008, A1. Location in patent: Page/Page column 83-84
[5] Patent: US2009/98086, 2009, A1. Location in patent: Page/Page column 59

4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine(98141-42-5)Related Product Information

• 4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine
• 4,6-DICHLORO-1H-PYRAZOLO[3,4-D]PYRIMIDINE
• 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE