Phenol → HCID 90408710, compound

HRID 1521680Notes

Reaction equation

Br[C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:22]=[C:10]3[C:11](=[O:21])[N:12]([CH3:20])[C:13]4[N:14]([CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=4)[C:9]3=[N:8]2)=[CH:4][CH:3]=1.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1C(=O)CCC1.O.Cl[Cu]>[O:31]([C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:22]=[C:10]3[C:11](=[O:21])[N:12]([CH3:20])[C:13]4[N:14]([CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=4)[C:9]3=[N:8]2)=[CH:4][CH:3]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-(4-Bromobenzyl)-7,8-dihydro-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one (118 g, 304 mmol) is added into a suspension of phenol (57 g, 606 mmol) and cesium carbonate (200 g, 614 mmol) in NMP (900 mL), followed by 2,2,6,6-tetramethylheptane-3,5-dione (7 mL, 33.5 mmol) and CuCl (15 g, 152 mmol). The reaction mixture is heated at 120° C. under argon atmosphere for 10 h. After the completion of the reaction, the mixture is diluted with water (4 L), and then extracted with ethyl acetate. The combined organic phase is evaporated to dryness. The obtained crude product is purified by silica gel column chromatography to give 103 g of product (yield: 84%). MS (ESI) m/z 402.2 [M+H]+.

Workup

customAfter the completion of the reaction
extractionextracted with ethyl acetate
customThe combined organic phase is evaporated to dryness
customThe obtained crude product
customis purified by silica gel column chromatography

Sources & evidence

ORD record: ord-6d55e7b6a6ad4a5fa2db0b9c646a6988
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073936B2

Reaction notes

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