Water → HCID 69102284, compound

HRID 2217251Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1Br.[Cl-].C[Zn+].[CH3:28]COC(C)=O.O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg) and Pd(PPh3)4 (15 mg) in THF (1.0 ml), was added a solution of methylzinc chloride in THF (2.0M, 0.75 ml). The mixture was stirred at 25° C. for 7.5 hours and then heated at 60° C. for 1.5 hours. After cooling, EtOAc and water were poured into the mixture, and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was crystallized form MeOH-IPE and dried in vacuo to give 5-(5-amino-6-methyl-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (95 mg).

Workup

temperatureheated at 60° C. for 1.5 hours
temperatureAfter cooling
customthe organic layer was separated
washwashed with water and brine
dry with materialdried over MgSO4
customThe solvent was removed under reduced pressure
customThe residue was crystallized
customform MeOH-IPE
customdried in vacuo

Sources & evidence

ORD record: ord-e2512f71e06f4df699d98ace4e854fa4
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407961B2

Reaction notes

Loading…