Sodium Carbonate → HCID 69331975, compound

HRID 915083Notes

Reaction equation

C([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[C:9]([C:25]([NH2:27])=[O:26])=[N:10][C:11]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)=[C:12](Cl)[N:13]=1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1B(O)O>O.O1CCOCC1.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>[NH2:7][C:8]1[C:9]([C:25]([NH2:27])=[O:26])=[N:10][C:11]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)=[C:12]([C:29]2[S:28][CH:32]=[CH:31][CH:30]=2)[N:13]=1

Participants

Conditions

Temperature: 102.5 °C

Procedure

Under nitrogen atmosphere, a solution of Na2CO3 (138 mg) in water (0.8 ml) was added to a suspension of 3-amino-5-chloro-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarboxamide (100 mg), 2-thienylboronic acid (104 mg) and tetrakis(triphenylphosphine)palladium (11.3 mg) in dioxane (2 ml) and the mixture was stirred at 100-105° C. for 4 hours. After addition of water (10 ml), a precipitate was collected by filtration and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v) to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-(2-thienyl)-2-pyrazinecarboxamide as a solid (85 mg).

Workup

filtrationa precipitate was collected by filtration
custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v)

Sources & evidence

ORD record: ord-5428d42da2ca4155b0f696e488d7a91a
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

Loading…