Ammonium fluoride → HCID 22125153, compound

HRID 1858276Notes

Reaction equation

HRID 1858276 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([S:18]([CH3:21])(=[O:20])=[O:19])=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:23]=2)[C:9]1=[O:47].[F-].[NH4+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([S:18]([CH3:21])(=[O:20])=[O:19])=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][OH:29])[CH:23]=2)[C:9]1=[O:47]

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 54384838HCID 54384838, compound

Product 1

HCID 22125153HCID 22125153, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 400 mg (0.55 mmol) of 3-(2-bromophenyl)-1-[3-(tert-butyldiphenylsilyloxymethyl)phenyl]-3,4-dihydro-7-methanesulfonyl-pyrimido[4,5-d]pyrimidin-2(1H)-one in 30 ml of methanol was treated with 400 mg (11 mmol) of ammonium fluoride and the mixture heated at reflux for 1 hour. The mixture was evaporated and the product purified by flash chromatography on silica gel eluting with dichloromethane/methanol in a ratio of 20:1. The product-containing fractions were combined and evaporated to afford 257 mg (96%) of 3-(2-bromophenyl)-3,4-dihydro-1-[3-(hydroxymethyl)phenyl]-7-methanesulfonyl-pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =490].

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. customThe mixture was evaporated
  4. customthe product purified by flash chromatography on silica gel eluting with dichloromethane/methanol in a ratio of 20:1
  5. customevaporated

Sources & evidence

ORD record
ord-e7d7cc232e94420596f22d4ae10e954d
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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