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

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N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine Basic information
Product Name:N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Synonyms:7H-Pyrrolo[2,3-d]pyriMidin-4-aMine, N-Methyl-N-[(3R,4R)-4-Methyl-1-(phenylMethyl)-3-piperidinyl]-;1H-Pyrrolo[2,3-d]pyriMidin-4-aMine,N-Methyl-N-[(3R,4R)-4-Methyl-1-(phenylMethyl)-3-piperidinyl]-;Tasocitinib Intermediate;-1-Benzyl-4-methylpiperidin-3-yl);N-((3R,4R);Tofacitinib impurity 6/N-Methyl-N-[(3R,4R)-4-methyl-1-(phenylmethyl)-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine;Tofacitinib-10;(3R, 4R)-(1-benzyl-4-methyl-piperidin-3-yl) -methyl- (7H-pyrrolo [2,3-d] pyrimidin-4-yl) -amine
CAS:477600-73-0
MF:C20H25N5
MW:335.45
EINECS:
Product Categories:API
Mol File:477600-73-0.mol
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine Structure
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical Properties
Melting point 67-69℃
density 1.205±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka13.36±0.50(Predicted)
InChIInChI=1S/C20H25N5/c1-15-9-11-25(12-16-6-4-3-5-7-16)13-18(15)24(2)20-17-8-10-21-19(17)22-14-23-20/h3-8,10,14-15,18H,9,11-13H2,1-2H3,(H,21,22,23)/t15-,18+/m1/s1
InChIKeyUMWNXPTXDOVDFE-QAPCUYQASA-N
SMILESC1=NC(N(C)[C@@H]2[C@H](C)CCN(CC3=CC=CC=C3)C2)=C2C=CNC2=N1
Safety Information
MSDS Information
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine Usage And Synthesis
UsesN-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine is an important pharmaceutical intermediate used for the synthesis of tofacitinib. Tofacitinib is a Janus kinase (JAK) inhibitor drug used to treat rheumatoid arthritis and psoriatic arthritis.
SynthesisN-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine is prepared by the reaction of 4-chloropyrrolopyrimidine and (3R,4R)-1-benzyl-N,4-dimethylpiperidin-3-amine dihydrochloride. The specific synthesis steps are as follows:
The reaction flask is added to sodium hydroxide (10.0g, 250mmol), water and dissolved, make 10% of the solution, adding acetone to another reaction bottle 80g, the toluene sulfonyl chloride (38.13g, 200mmol), after stirring to dissolve, then adding 4-chloro pyrrolo pyrimidine (15.36g, 100mmol), stirring mixing, cooling to 0 °C the following, dropping sodium hydroxide solution, the temperature is controlled at 5 °C the following, completion of the dropping, heating, to control the temperature to 20-30 °C stirring within the range of the reaction, to the reaction end after TLC monitoring, filtering, to get the product into the reaction bottle, adding water 200 ml, (3R, 4R)-cis-1-benzyl-4-methyl-3-methylamino-piperidine dihydrochloride (21.33g, 105mmol), stirring to dissolve, then adding potassium carbonate (82.93g, 600mmol), stirring, heating 95 °C, TLC monitoring to the reaction end of the, cooling to 45-55°C, by adding acetonitrile, preserving heat and stirring 1 hour, cooling to room temperature, crystallization, filtration, washing, the wet articles in added in the reaction bottle, adding dimethyl sulfoxide 250 ml, by adding 50% sodium hydroxide solution to 250 ml, stirring and heating 95 °C, TLC monitoring to the reaction end rear, layered, water extraction once with dimethyl sulfoxide, merger dimethyl asian sulphone level, cooling to 75-85°C, water slowly under stirring, the stirring cooling to room temperature, filtering, washing, 50% ethanol washing, filtering, drying, be [(3R, 4R) - 1 benzyl-4-methyl-piperidin-3-yl]-methyl-(7H-pyrrolo [2,3-d] pyrimidin-4-yl)-amine 25.83g, yield 77.0%, optical purity 99.8% (HPLC method).
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine synthesis
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine Preparation Products And Raw materials
Tag:N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine(477600-73-0) Related Product Information
N-Methyl-N-nitrosotoluene-4-sulphonamide 4-(Hydroxyamino)-4-oxobutanoic acid Tofacitinib Impurity 3 Tofacitinib Impurity 6 3-Amino-4-methylpyridine N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine Methyl (1-benzyl-4-Methylpiperidin-3-yl)carbaMate 13-Deoxyepirubicin 3-((3R,4S)-4-Methyl-3-(Methyl(7H-pyrrolo[2,3-d]pyriMidin-4-yl)aMino)piperidin-1-yl)-3-oxopropanenitrile 1-[2-(2-methoxyphenoxy)ethylamino]-3-(9-methylcarbazol-4-yl)oxypropan-2-ol:hydrochloride Methyl (4-Methylpiperidin-3-yl)carbaMate 3-((3S,4R)-4-Methyl-3-(Methyl(7H-pyrrolo[2,3-d]pyriMidin-4-yl)aMino)piperidin-1-yl)-3-oxopropanenitrile 3-PiperidinaMine, 1-acetyl-N,4-diMethyl-N-1H-pyrrolo[2,3-d]pyriMidin-4-yl-, (3R,4R)- (9CI) 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 7H-Pyrrolo[2,3-d]pyriMidin-4-aMine, N-Methyl-N-[(3R,4R)-4-Methyl-1-(phenylMethyl)-3-piperidinyl]-7-[(4-Met hylphenyl)sulfonyl]- 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE 2,4-Dichloro-7H-pyrrolo2,3-dpyrimidine 3-Methoxycarbonylamino-4-methylpyridine