Hydrochloric Acid → HCID 18619234, compound

HRID 1862259Notes

Reaction equation

HRID 1862259 reaction equation
N(OCCC(C)C)=O.N[C:10]1[CH:30]=[C:29]([F:31])[C:28]([N:32]2[C:37](=[O:38])[CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[N:34]([CH3:43])[C:33]2=[O:44])=[CH:27][C:11]=1[O:12][C:13]1[C:14]([O:20][CH:21]([C:23]([O:25][CH3:26])=[O:24])[CH3:22])=[N:15][C:16]([CH3:19])=[N:17][CH:18]=1.[ClH:45]>[Cu]Cl.[Cu](Cl)Cl.C(#N)C>[Cl:45][C:10]1[CH:30]=[C:29]([F:31])[C:28]([N:32]2[C:37](=[O:38])[CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[N:34]([CH3:43])[C:33]2=[O:44])=[CH:27][C:11]=1[O:12][C:13]1[C:14]([O:20][CH:21]([C:23]([O:25][CH3:26])=[O:24])[CH3:22])=[N:15][C:16]([CH3:19])=[N:17][CH:18]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 18619211HCID 18619211, compound

Product 1

HCID 18619234HCID 18619234, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Isoamyl nitrite is added to a mixture of 5-{2-amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-{1-(methoxycarbonyl)ethoxy}-2-methylpyrimidine, copper(I) chloride, copper(II) chloride and acetonitrile dropwise at room temperature, and the mixture is stirred for 1 hour. This reaction solution is poured into 2% hydrochloric acid, and extracted with ethylacetate. The organic layer is washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue is subjected to silica gel column chromatography to obtain 5-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-{1-(methoxycarbonyl)ethoxy}-2-methylpyrimidine [present compound4-76].

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic layer is washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-52e427ca66c84880ae80ef86f0e491f5
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

Loading…