Diisopropylethylamine → HCID 136247181, compound

HRID 1022441Notes

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

Participants

Conditions

Temperature: 140 °C

Procedure

A microwave reaction vial was charged with 2-chloro-7-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate A) (25 mg, 0.13 mmol), 4-(4-fluorophenyl)piperidine hydrochloride (35.2 mg, 0.16 mmol), and N,N-diisopropylethylamine (52.8 mg, 0.41 mmol) in ethanol (1.5 mL). The vial was sealed and then heated in the microwave at 140° C. for 15 min. At this time, the resulting mixture was concentrated in vacuo. Flash chromatography (20/1 methylene chloride/methanol) afforded 2-[4-(4-fluoro-phenyl)-piperidin-1-yl]-7-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (44.4 mg, 36%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.5-1.7 (m, 2H) 1.8 (d, J=11.55 Hz, 2H) 2.8 (br. s., 1H) 2.9 (t, J=12.05 Hz, 2H) 3.5 (s, 3H) 4.5 (d, J=13.05 Hz, 2H) 6.2 (d, J=3.51 Hz, 1H) 6.7 (d, J=3.26 Hz, 1H) 7.1 (t, J=8.78 Hz, 2H) 7.3 (dd, J=8.53, 5.52 Hz, 2H) 10.7 (s, 1H). LC-MS calcd. for C18H20FN4O [(M+H)+] 327, obsd. 327.0.

Workup

customA microwave reaction
customThe vial was sealed
concentrationAt this time, the resulting mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-9845edea8db54b74977c7c389fb4adb3
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722661B2

Reaction notes

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