Hydrochloric Acid → HCID 18619155, compound

HRID 1862308Notes

Reaction equation

HRID 1862308 reaction equation
N(OCCC(C)C)=O.N[C:10]1[CH:28]=[C:27]([F:29])[C:26]([N:30]2[C:35](=[O:36])[CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[N:32]([CH3:41])[C:31]2=[O:42])=[CH:25][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:17][CH:18]=1.[ClH:43]>[Cu]Cl.[Cu](Cl)Cl.C(#N)C>[Cl:43][C:10]1[CH:28]=[C:27]([F:29])[C:26]([N:30]2[C:35](=[O:36])[CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[N:32]([CH3:41])[C:31]2=[O:42])=[CH:25][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:17][CH:18]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl Nitrite2×HCID 18619252HCID 18619252, compound

Product 1

HCID 18619155HCID 18619155, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

0.3 g of isoamyl nitrite was added to a mixture of 0.83 g of 5-{2-amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine, 0.34 g of copper(I) chloride, 0.69 g of copper(II) chloride and 3 ml of acetonitrile dropwise at room temperature, and the mixture was stirred for 1 hour. 0.3 g of isoamyl nitrite was added to the mixture, and stirred for 20 minutes. This reaction solution was poured into 2% hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.52 g of 5-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine [present compound 7-17].

Workup

  1. stirringstirred for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c562f5962d86436c88912aa532538bef
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

Loading…