HCID 86592984, compound → HCID 86592986, compound

HRID 2181360Notes

Reaction equation

HRID 2181360 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH:23]=[CH:24][C:25]([O:27][CH3:28])=[O:26])=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[S:11][C:5]=2[N:4]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:3]1=[O:33]>[Pd].C(O)C>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:20])([F:21])[F:22])[S:11][C:5]=2[N:4]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:3]1=[O:33]

Participants

4

Reactant 1

HCID 86592984HCID 86592984, compound

Product 1

HCID 86592986HCID 86592986, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A slurry of 10% palladium on charcoal in ethanol was added to a solution of 3-[1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]thieno[2,3-d]pyrimidin-5-yl]-2-propenoic acid, methyl ester, (2.17 g, Example 3 step a)) in ethanol (75 ml) and hydrogenated at 4 bar for 48 hours. The solution was filtered through a glass fibre filter and the filtrate concentrated under reduced pressure. The residue was purified by flash silica chromatography eluting with 1% ethanol in dichloromethane to give the sub-title compound as a white solid (1.27 g).

Workup

  1. filtrationThe solution was filtered through a glass fibre
  2. filtrationfilter
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by flash silica chromatography
  5. washeluting with 1% ethanol in dichloromethane

Sources & evidence

ORD record
ord-2ce930904a434ddbb554bd34dde782b3
Source dataset
uspto-grants-2005_05
Patent number
US06890923B2

Reaction notes

Loading…