N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine synthesis
- Product Name:N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
- CAS Number:477600-74-1
- Molecular formula:C13H19N5
- Molecular Weight:245.32
![1-Piperidinecarboxylic acid, 4-methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-, 1,1-dimethylethyl ester, (3R,4R)-](/CAS/20200611/GIF/1450663-24-7.gif)
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Yield:477600-74-1 95%
Reaction Conditions:
with zinc dibromide in dichloromethane; for 12 h;
Steps:
tert-Butyl(3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate(1-NH)
The 1-Boc (0.106 mmol) in CH2Cl2(3 mL) was added ZnBr2 (0.170 g, 0.742 mmol). After reaction for 12 h, the mixture was filtered and evaporatedunder reduced pressure. The crude solid was purified by flash chromatography(100-200 mesh silica-gel, PE:EtOAc, 1:5, Rf = 0.4) affording 1-NH in 95% yield as a colorless solid. [a]D = +5.8 (c 1.0, MeOH). Mp 158-159 oC. 1H NMR (400 MHz, CDCl3), d: 1.10(d, J 7.0 Hz, 3H), 1.58-1.81 (m, 2H),1.82-1.99 (m, 1H), 2.44-2.59 (m, 1H), 2.78-3.10 (m, 3H), 3.25-3.40 (m, 1H), 3.46(s, 3H), 4.85-5.00 (m, 1H), 6.59 (d, J3.5 Hz, 1H), 7.05 (d, J 3.5 Hz, 1H),8.33 (s, 1H), 10.50 (br s, 1H). 13C NMR (100 MHz, CDCl3),d: 14.1, 32.3, 33.3, 34.7, 42.3, 46.2, 56.4, 102.5, 103.1, 120.2,151.3, 152.1, 158.0. HRMS (ESI): m/z calc. for [C13H19N5+ H]+ 246.1719; found: 246.1721. Anal. calcd for C13H19N5:C, 63.65; H, 7.81; N, 28.55. Found: C, 63.82; H, 7.84; N, 28.65.Nigam, S. C., Mann, A., Taddei, M., Wermuth, C.-G. Synth. Commun. 1989, 19, 3139
References:
Maricán, Adolfo;Simirgiotis, Mario J.;Santos, Leonardo S. [Tetrahedron Letters,2013,vol. 54,# 37,p. 5096 - 5098] Location in patent:supporting information
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