1-(4-Pyridyl)piperazine → HCID 136247062, compound

HRID 1022435Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-chloro-7-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate A) (50.1 mg, 273 μmol) in ethanol (730 μL) was treated with 1-(pyridin-4-yl)piperazine (51.8 mg, 317 μmol) and N,N-diisopropylethylamine (46.7 mg, 63.10 μL, 361 μmol). The reaction stirred at 100° C. overnight. At this time, the reaction was diluted with methanol and methylene chloride and concentrated in vacuo onto Celite®. Flash chromatography (4 g silica gel column, 10% methanol/methylene chloride) afforded 7-methyl-2-(4-pyridin-4-yl-piperazin-1-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (43 mg, 50.8%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.48 (d, J=4.33 Hz, 4H) 3.57 (s, 3H) 3.69 (d, J=6.03 Hz, 4H) 6.25 (d, J=3.39 Hz, 1H) 6.78 (d, J=3.20 Hz, 1H) 6.91 (d, J=6.97 Hz, 2H) 8.19 (d, J=6.40 Hz, 2H) 10.90 (s, 1H). LC-MS calcd. for C16H19N6O [(M+H)+] 311, obsd. 311.1.

Workup

concentrationconcentrated in vacuo onto Celite®

Sources & evidence

ORD record: ord-a0c024694ec244ddb6aa425c840941d4
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722661B2

Reaction notes

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