Tetrabutylammonium Fluoride → HCID 22125171, compound

HRID 1858279Notes

Reaction equation

HRID 1858279 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:33][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:27]=3)[C:15](=[O:25])[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Br:24])[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:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][OH:33])[CH:27]=3)[C:15](=[O:25])[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Br:24])[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 22124965HCID 22124965, compound

Product 1

HCID 22125171HCID 22125171, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.5 g (2 mmol) of 7-anilino-3-(2-bromophenyl)-1-[3-((tert-butyldiphenylsilyloxy)methyl)phenyl]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one in 30 ml of tetrahydrofuran was treated with 2.5 ml (2.5 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 dichloromethane/methanol 100:1 as eluent. Product-containing fractions were evaporated to give 550 mg (55%) of 7-anilino-3-(2-bromophenyl)-3,4-dihydro-1-[3-(hydroxymethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 136° C. [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
  11. customProduct-containing fractions were evaporated

Sources & evidence

ORD record
ord-adc068064fd1472b9b79172d5cab3e1e
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

Loading…