HCID 86667461, compound → HCID 68007076, compound

HRID 1027791Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]([C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][N:3]=1.[Br-].[CH2:21]([Zn+])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O1CCCC1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O1CCCC1>[CH2:21]([C:2]1[N:10]=[C:9]2[C:5]([N:6]([C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a mixture of 2-chloro-9-methyl-7-(pyrrolidin-1-ylcarbonyl)-7,9-dihydro-8H-purine-8-one <the compound of Reference Example 16> (200 mg), bis(tri-tert-butylphosphine)palladium (18 mg) and tetrahydrofuran (1.0 ml) was added dropwise 0.5 mol/L benzyl zinc bromide/tetrahydrofuran solution (2.14 ml) under nitrogen atmosphere and the mixture was stirred at 130° C. under microwave irradiation for 1 hour. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0˜90/10). The obtained crude solids were recrystallized from a mixed solution of ethyl acetate and hexane to give the title compound 68 mg.

Workup

filtrationThe reaction mixture was filtered through Celite
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0˜90/10)
customThe obtained crude solids
customwere recrystallized from a mixed solution of ethyl acetate and hexane

Sources & evidence

ORD record: ord-b2461a9f08e44607a225ce974136a7ce
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735406B2

Reaction notes

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