Ammonium Chloride → HCID 22269958, compound

HRID 488410Notes

Reaction equation

HRID 488410 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Br:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]2[C:39]3[C:34](=[CH:35][C:36]([O:43][CH2:44][CH2:45][CH2:46][O:47][Si](C(C)(C)C)(C)C)=[C:37]([N+:40]([O-:42])=[O:41])[CH:38]=3)[N:33]=[CH:32][N:31]=2)[CH:26]=[CH:27][CH:28]=1.[Cl-].[NH4+]>O1CCCC1>[Br:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]2[C:39]3[C:34](=[CH:35][C:36]([O:43][CH2:44][CH2:45][CH2:46][OH:47])=[C:37]([N+:40]([O-:42])=[O:41])[CH:38]=3)[N:33]=[CH:32][N:31]=2)[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 22269956HCID 22269956, compound

Product 1

HCID 22269958HCID 22269958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.60 g tetrabutylammonium fluoride-trihydrate are added to 2.50 g of 4-[(3-bromophenyl)amino]-7-[3-(tert. butyldimethylsilyloxy)-propyloxy]-6-nitro-quinazoline in 25 ml of tetrahydrofuran. The reaction mixture is stirred for about 2 hours at ambient temperature. After the cleavage is complete, the reaction mixture is combined with 150 ml of a 2% ammonium chloride solution and cooled in the ice bath. A yellow precipitate is formed which is suction filtered and washed with water. The precipitate, while still damp, is dissolved in methylene chloride/methanol (6:4), dried over sodium sulphate and concentrated by evaporation. The yellow residue is stirred with a little petroleum ether and suction filtered, washed with petroleum ether and dried in vacuo. Yield: 1.29 g (66% of theory) Rf value: 0.63 (silica gel, methylene chloride/methanol=9:1) Mass spectrum (ESI*): m/z=417, 419 [M−H]−

Workup

  1. customA yellow precipitate is formed which
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionThe precipitate, while still damp, is dissolved in methylene chloride/methanol (6:4)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation
  7. stirringThe yellow residue is stirred with a little petroleum ether and suction
  8. filtrationfiltered
  9. washwashed with petroleum ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-7aafee2d298a493a8a36f9582742641e
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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