Acetyl chloride → N-[6-(2-Furyl)-5-pyrimidin-4-ylpyrazin-2-yl]acetamide

HRID 1710706Notes

Reaction equation

[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:13]=[C:12]([NH2:14])[CH:11]=[N:10][C:9]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][N:16]=1.[C:21](Cl)(=[O:23])[CH3:22]>CN(C=O)C.C(OCC)(=O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:13]=[C:12]([NH:14][C:21](=[O:23])[CH3:22])[CH:11]=[N:10][C:9]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (42 mg, 1.05 mmol) was added to a stirred solution of 6-(2-furyl)-5-pyrimidin-4-ylpyrazin-2-amine (Example 8, 100 mg, 0.42 mmol) in DMF (4 mL) at 0° C. under nitrogen. The solution was allowed to stir for 30 min. at 0° C. Acetyl chloride (60.0 μL, 0.84 mmol) was then added and the reaction mixture was warmed up to room temperature and stirred for 3 days. The reaction was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by silica gel flash chromatography (50% ethyl acetate in hexanes to 75% ethyl acetate in hexanes). Concentration in vacuo of the product-rich fractions provided the titled compound as a pale-yellow solid (8 mg, 7%).

Workup

temperaturethe reaction mixture was warmed up to room temperature
stirringstirred for 3 days
washwashed with water
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
customevaporated
customThe residue was purified by silica gel flash chromatography (50% ethyl acetate in hexanes to 75% ethyl acetate in hexanes)
concentrationConcentration in vacuo of the product-rich fractions

Sources & evidence

ORD record: ord-895fa5cbd86d4adcac5ad8a59a4dda19
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790728B2

Reaction notes

Loading…