3-Chloropyridazine → 5-(4-Chloro-phenyl)-1-phenyl-6-(4-pyridazin-3-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693565Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:20](=[O:21])[C:19]3[CH:22]=[N:23][N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:18]=3[N:17]=[C:16]2[C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][CH:32]=2)=[CH:11][CH:10]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:20](=[O:21])[C:19]3[CH:22]=[N:23][N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:18]=3[N:17]=[C:16]2[C:31]2[CH:32]=[CH:33][C:34]([C:2]3[N:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[CH:35][CH:36]=2)=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 112749893-Chloropyridazine

HCID 578979725-(4-Chloro-phenyl)-1-phenyl-6-[4-(4,4,5,5-tetramethyl [1,3,2]dioxaborolan-2-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 578980095-(4-Chloro-phenyl)-1-phenyl-6-(4-pyridazin-3-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

5-(4-Chloro-phenyl)-1-phenyl-6-(4-pyridazin-3-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one is prepared from 3-chloropyridazine and 5-(4-chloro-phenyl)-1-phenyl-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one by using the same method described in example 338. The crude product is purified by flash column chromatography (silica gel, 0˜70% EtOAc/hexane). 1H NMR (CDCl3) δ (ppm) 9.19 (b, 1H), 8.34(s, 1H), 8.15(d, 2H), 8.02(d, 2H), 7.84(d, 1H), 7.51(m, 5H), 7.33 (m, 3H), 7.15(d, 2H). HPLC-MS calculated C27H17ClN6O (M+1+): 477.1. Found: 477.1.

Workup

customThe crude product is purified by flash column chromatography (silica gel, 0˜70% EtOAc/hexane)

Sources & evidence

ORD record: ord-f83c279bfa104de285af8d427cba3f24
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158634B2

Reaction notes

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