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

HRID 44413

Reaction equation

HRID 44413 reaction equation
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH3:24])[CH:20]([NH:25][CH3:26])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH3:24])[CH:20]([N:25]([CH3:26])[C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 99438891-benzyl-N,4-dimethylpiperidin-3-amineHCID 178418725HCID 178418725, compound

Product 1

HCID 12084829N-(1-Benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 50%

Conditions

Temperature
100 °C

Procedure

A solution of 4-chloropyrrolo[2,3-d]pyrimidine (2.4 grams, 15.9 mmol), prepared by the method of Davoll, J. Am. Chem. Soc., 82, 131 (1960), which is incorporated by reference in its entirety, and the product from Method A (1.7 grams, 7.95 mmol) dissolved in 2 equivalents of triethylamine was heated in a sealed tube at 100° C. for 3 days. Following cooling to room temperature and concentration under reduced pressure, the residue was purified by flash chromatography (silica; 3% methanol in dichloromethane) affording 1.3 grams (50%) of the title compound as a colorless oil. LRMS: 336.1 (M+1).

Workup

  1. temperatureFollowing cooling to room temperature
  2. concentrationconcentration under reduced pressure
  3. customthe residue was purified by flash chromatography (silica; 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-90ce4c8ad50f4e4aa7af55ff18e28333
Source dataset
uspto-grants-2013_09
Patent number
US08541426B2

Linked notes

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