Sodium Iodide → HCID 19098110, compound

HRID 1975666Notes

Reaction equation

HRID 1975666 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:16]([C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)[OH:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].C[O-].[Li+].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[N:44]([C:45]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:43]=[N:42][N:41]=2)=[CH:30][CH:29]=1.[I-].[Na+]>CN(C)C=O>[CH2:1]([C:5]1[N:14]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[N:44]([C:45]([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)([C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[N:43]=[N:42][N:41]=3)=[CH:32][CH:33]=2)[C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[OH:17])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 4177230Lithium methanolateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 178441855HCID 178441855, compound

Product 1

HCID 19098110HCID 19098110, compoundYield 154%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 500 mg of 2-butyl-6-(2-furanylhydroxymethyl)-4(1H)-quinazolinone in 8 ml of N,N-dimethylformamide is stirred while 63.64 mg of lithium methoxide is added followed by 1.87 g of 5-[4'-(bromomethyl)[1,1'biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole. After stirring for 10 minutes, 251.25 mg of sodium iodide is added followed by heating in an oil bath at 55° C. for 18 hours. The volatiles are evaporated in vacuo to a residue which partitioned between ethyl acetate and water. The organic layer is washed with brine, dried with anhydrous Na2SO4 and the volatiles evaporated to afford 2.0 g of a dark residue. The residue is purified by chromatography on silica gel with (2.25:1)hexanes:ethyl acetate as solvent to afford 815 mg of the desired product as a white foam. Fab Mass Spec 797 (M+Na).

Workup

  1. additionis added
  2. customThe volatiles are evaporated in vacuo to a residue which
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer is washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customthe volatiles evaporated

Sources & evidence

ORD record
ord-a2e607c4647543898b766463bd01231d
Source dataset
uspto-grants-1994_02
Patent number
US05288720

Reaction notes

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