4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine Chemical Properties

Melting point:

130 °C

Boiling point:

301.5±22.0 °C(Predicted)

Density 

1.43±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Dichloromethane, Ethyl Acetate, Methanol

pka

3.16±0.30(Predicted)

form 

Solid

color 

Light Brown

InChI

InChI=1S/C7H6ClN3/c1-11-3-2-5-6(8)9-4-10-7(5)11/h2-4H,1H3

InChIKey

BJGDLOLPALCTJQ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HS Code 

2933998090

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine Usage And Synthesis

Chemical Properties

Light Brown Solid

Uses

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine is used in the preparation of indoline derivatives as PERK inhibitors.

Synthesis

The general procedure for the synthesis of 4-chloro-7-methylpyrrolo[2,3-D]pyrimidine from 4-chloropyrrolopyrimidine and iodomethane was as follows: iodomethane (12.2 mL, 195 mmol) was added slowly and dropwise to a solution containing 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (15.0 g, 97.7 mmol) and cesium carbonate (47.7 g, 146.5 mmol) in a N,N-dimethylformamide (DMF, 200 mL) solution. The reaction mixture was stirred at room temperature for 1 h. The reaction was subsequently quenched with deionized water (500 mL). The reaction mixture was extracted with ethyl acetate (3 x 200 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Purification of the crude product by fast column chromatography (silica gel, gradient elution with ethyl acetate:hexane, 2:8 to 3:7) afforded 4-chloro-7-methylpyrrolo[2,3-D]pyrimidine as an off-white solid (15.4 g, 94% yield). Mass Spectrometry (MS): m/z 168.5 ([M+H]+); High Performance Liquid Chromatography (HPLC) retention time (Rf): 3.45 min (HPLC method 4); HPLC purity: 96%.

References

[1] Patent: WO2004/56830, 2004, A1. Location in patent: Page 93
[2] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 16, p. 2153 - 2157
[3] Patent: WO2017/46739, 2017, A1. Location in patent: Page/Page column 89
[4] Patent: WO2018/194885, 2018, A1. Location in patent: Page/Page column 15
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7193 - 7207

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine(7781-10-4)Related Product Information

• 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
• 7-BENZYL-4-CHLORO-5,6-DIPHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 7-ALLYL-4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE
• 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE
• ETHYL 4-CHLORO-5-METHYL-7-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE-6-CARBOXYLATE
• 4-CHLORO-7-(3-CHLORO-4-METHYLPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 6-CHLORO-7-DEAZA-9-(2',3',5'-TRI-O-ACETYL-BETA-D-RIBOFURANOSYL)PURINE
• 4-CHLORO-7-(4-FLUOROPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 4-CHLORO-7-(4-CHLOROPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 4-CHLORO-7-(4-METHYLPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 6-Chloro-7-deazapurine-b-D-riboside
• 4-CHLORO-5-PHENYL-7-[3-(TRIFLUOROMETHYL)PHENYL]-7H-PYRROLO[2,3-D]PYRIMIDINE
• 6-Chloro-7-deaza-9-(5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-b-D-ribofuranosyl)purine
• 4-CHLORO-7-(4-METHOXYPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 7-(4-BROMOPHENYL)-4-CHLORO-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 4-CHLORO-7-(2-FURYLMETHYL)-5,6-DIMETHYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 4-CHLORO-7-(3-CHLOROPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• 4-CHLORO-7-(4-ETHOXYPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE