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

Melting point:

145.0 to 149.0 °C

Boiling point:

505.3±60.0 °C(Predicted)

Density 

1.49

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

powder to crystal

pka

1.73±0.30(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C13H10ClN3O2S/c1-9-2-4-10(5-3-9)20(18,19)17-7-6-11-12(14)15-8-16-13(11)17/h2-8H,1H3

InChIKey

BTOJSYRZQZOMOK-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C2C=CN(S(C3=CC=C(C)C=C3)(=O)=O)C2=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933599590

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

Uses

4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine is a reagent in the synthesis of (+)-tofacitinib, a selective Janus kinase 3 inhibitor (JAK3) and an immunosuppressant drug.

Synthesis

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (2kg, 12.96mol) and dichloromethane (40L) were added to the reaction flask at room temperature, stirred and dissolved. Triethylamine (3.88 kg, 38.4 mol) and 4-dimethylamino pyridine (157.6 g, 1.28 mol) were added in that order, and after stirring and dissolved, p-toluenesulfonyl chloride (2.6 kg, 13.6 mol) was added dropwise at 0 °C. The chloromethane (30 L) solution was added dropwise, and the mixture was stirred at room temperature for 30 min. After the TLC was applied, the mixture was washed with water (16L×3). 4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (3.9 kg, yield 97.7%) was obtained after drying under reduced pressure.

4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine(479633-63-1)Related Product Information

• N-Methyl-N-((3S,4S)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• 7H-Pyrrolo[2,3-d]pyriMidin-4-aMine, N-Methyl-N-[(3R,4R)-4-Methyl-1-(phenylMethyl)-3-piperidinyl]-7-[(4-Met hylphenyl)sulfonyl]-
• (3R,4R)-1-benzyl-N,4-dimethylpiperidin-3-amine dihydrochloride
• DEAZAPURINE
• 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
• Trifluorothymine
• 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• 2,4-DICHLORO-7H-PYRROLO2,3-DPYRIMIDINE
• 4-Amino-7H-pyrrolo[2,3-d]pyrimidine
• 2-Amino-4-chloropyrrolo[2,3-d]pyrimidine
• 2-Thiouracil
• 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE
• 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine
• Pyrrolo[2,3-d]pyrimidin-4-ol
• N4-Benzoylcytosine
• 4-Aminopyrazolo[3,4-d]pyrimidine
• 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
• Tofacitinib Impurity T