N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Base Information

• Chemical Name: N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• CAS No.: 477600-74-1
• Molecular Formula: C13H19N5
• Molecular Weight: 245.327
• Mol file: 477600-74-1.mol

Synonyms:1H-Pyrrolo[2,3-d]pyrimidin-4-amine,N-methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]- (9CI);(3R,4R)-Methyl{(4-methylpiperidin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-4-yl)}amine;

Chemical Property of N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Chemical Property:

• Refractive Index: 1.636
• PKA: 13.36±0.50(Predicted)
• PSA: 56.84000
• Density: 1.198 g/cm³
• LogP: 1.72090
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Aqueous Acid (Slightly), Methanol (Slightly), Water (Slightly, Heated)

Purity/Quality:

99.0%, High purity. ^*data from raw suppliers

TFG ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Methyl-N-((3S,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine, is an intermediate in the synthesis of (3S,4R)-Tofacitinib (T528010), an enantiopure stereoisomer of the drug, Janus kinase 3(Jak3) inhibitor (CP-690,550) that has been found to inhibit selected members of the STE7 and STE20 subfamily of kinases.

Technology Process of N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

There total 72 articles about N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-2-chloro-N-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine (923036-25-3) → tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (477600-74-1)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In water; at 65 - 75 ℃; for 3h; under 1551.49 Torr; Inert atmosphere;

Reference yield: 95.0%

(3R,4R)-tert-butyl 4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (1450663-24-7) → tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (477600-74-1)

Guidance literature:

With zinc dibromide; In dichloromethane; for 12h;

DOI:10.1016/j.tetlet.2013.07.042

Reference yield: 93.3%

((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amine → tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (477600-74-1)

Guidance literature:

With palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; at 45 ℃; under 6000.6 Torr;

DOI:10.1002/cmdc.201402252

upstream raw materials:

(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-2-chloro-N-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine

(S)-5-hydroxypiperidin-2-one

(5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one

7-deazaadenine

Downstream raw materials:

tasocitinib

Tofacitinib citrate

tofacitinib hemi-citrate

tofacitinib citrate

Refernces

• 1、 -. "Process for the preparation of tofacitinib and intermediates thereof". Page/Page column 15-16. . Retrieved 2021/05/07.
• 2、 -. "Preparation method of tofacitinib hydrolysis impurity". Paragraph 0043-0044. . Retrieved 2021/03/31.