Tetrabutylammonium Fluoride → HCID 22125111, compound

HRID 1858259Notes

Reaction equation

HRID 1858259 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][O:35][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:28]=3)[C:15](=[O:26])[N:16]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][OH:35])[CH:28]=3)[C:15](=[O:26])[N:16]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22124987HCID 22124987, compound

Product 1

HCID 22125111HCID 22125111, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.2 g (1.7 mmol) of 7-anilino-1-[3-(2-(tert-butyldiphenyl-silyloxy)ethyl)phenyl]-3-(2-chloro-6-methylphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 30 ml of tetrahydrofuran was treated with 2.25 ml (2.25 mmol) of tetrabutylammonium fluoride (1M in tetrahydrofuran). The mixture was heated at reflux for 5 hours, cooled and evaporated. The residue was partitioned between 50 ml of ethyl acetate and 50 ml of 2M aqueous hydrochloric acid. The organic phase was washed with 40 ml of water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using a gradient elution from dichloromethane/methanol 100:1 to dichloromethane/methanol 100:5. Product-containing fractions were evaporated to give 350 mg (42%) of 7-anilino-3-(2-chloro-6-methylphenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a gum. [Mass spectrum (ESI) MH+ =486].

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was partitioned between 50 ml of ethyl acetate and 50 ml of 2M aqueous hydrochloric acid
  6. washThe organic phase was washed with 40 ml of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica gel using
  11. washa gradient elution from dichloromethane/methanol 100:1 to dichloromethane/methanol 100:5
  12. customProduct-containing fractions were evaporated

Sources & evidence

ORD record
ord-c374661a3a264d75893969fb42fe12eb
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

Loading…