Acetic Acid → N-Methyl-N-[(3R,4R)-4-methylpiperidin-3-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2069002Notes

Reaction equation

C(O)(=O)C.C([N:12]1[CH2:17][CH2:16][C@@H:15]([CH3:18])[C@@H:14]([N:19]([CH3:29])[C:20]2[C:21]3[CH:28]=[CH:27][NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH2:13]1)C1C=CC=CC=1.[H][H].ClCCl>C(O)(C)C.O.[OH-].[OH-].[Pd+2]>[CH3:29][N:19]([C@@H:14]1[C@H:15]([CH3:18])[CH2:16][CH2:17][NH:12][CH2:13]1)[C:20]1[C:21]2[CH:28]=[CH:27][NH:26][C:22]=2[N:23]=[CH:24][N:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Palladium hydroxide on carbon (50 mg), and acetic acid (44 mg, 0.72 mmol, 1.00 equiv.) were added to a solution of N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (250 mg, 0.67 mmol, 1.00 equiv.) in isopropanol/water (10 mL/2 mL). After hydrogen gas was introduced, the resulting mixture was stirred at about 50° C. for about 16 hours. After filtering the mixture, the pH value of the filtrate was adjusted to 8 by adding sodium hydroxide. Standard extractive workup with dichloromethane (3×20 mL) afforded the title product as an off-white solid (140 mg; yield=81%) 1H NMR (300 MHz, CDCl3) δ: 10.60 (br s, 1H), 8.35 (s, 1H), 7.07 (d, J=3.6 Hz, 1H), 6.60 (d, J=3.6 Hz, 1H), 4.88-4.98 (m, 1H), 3.45 (s, 3H), 3.25-3.37 (m, 1H), 2.80-3.10 (m, 3H), 2.45-2.58 (m, 1H), 1.82-2.00 (m, 1H), 1.60-1.80 (m, 2H), 1.11 (d, J=7.2 Hz, 3H). LC-MS: m/z=246 (M+H)+.

Workup

filtrationAfter filtering the mixture
additionby adding sodium hydroxide

Sources & evidence

ORD record: ord-c0205c39e55a49e1a51dd51235047b18
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299084B2

Reaction notes

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