1,4-Benzodioxan-6-ylamine → N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-[2-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

HRID 1159876Notes

Reaction equation

CS([C:4]1[N:9]=[C:8]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)[CH:7]=[CH:6][N:5]=1)=O.[O:28]1[C:33]2[CH:34]=[CH:35][C:36]([NH2:38])=[CH:37][C:32]=2[O:31][CH2:30][CH2:29]1>C(O)C.Cl.C(Cl)Cl>[O:28]1[C:33]2[CH:34]=[CH:35][C:36]([NH:38][C:4]3[N:9]=[C:8]([C:10]4[C:11]([C:19]5[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=5)=[N:12][N:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=45)[CH:7]=[CH:6][N:5]=3)=[CH:37][C:32]=2[O:31][CH2:30][CH2:29]1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 3-[2-(methylsulfinyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine (1.32 g, 3.49 mmol) in ethanol (4.0 mL) is added 1,4-benzodioxan-6-amine (0.56 mL, 4.54 mmol) and conc. HCl (3 drops). The dark mixture is heated in a microwave apparatus at 160° C. for 20 min. The mixture is monitored, and heated for an additional 10 min. The mixture is diluted with DCM and concentrated to a brown foam. The crude material is purified by silica gel chromatography (30-50% EtOAc/hexanes) to give the desired product (1.09 g). 1H NMR (400 MHz, d6-DMSO) δ 9.36 (s, 1H), 8.88 (d, 1H, J=6.8), 8.45 (s, 1H), 8.28-8.31 (m, 3H), 8.01-8.03 (m, 1H), 7.72 (t, 1H, J=8.0), 7.47-7.51 (m, 1H), 7.13-7.18 (m, 2H), 6.97-6.95 (m, 1H), 6.63-6.65 (m, 2H), 4.14 (m, 1H), 7.13-7.18 (m, 2H), 6.95-6.97 (m, 1H), 6.63-6.65 (m, 2H), 4.14 (s, 4H).

Workup

temperatureheated for an additional 10 min
concentrationconcentrated to a brown foam
customThe crude material is purified by silica gel chromatography (30-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c23a4ea78c9147da91ac8c427408d4b1
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812022B2

Reaction notes

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