Methyl iodide → HCID 20079354, compound

HRID 486032Notes

Reaction equation

HRID 486032 reaction equation
[CH3:1]I.[H-].[Na+].[CH2:5]([C:9]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=2)[C:17](=[O:56])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:57]([OH:60])[CH2:58][CH3:59])[CH:15]=2)[N:10]=1)[CH2:6][CH2:7][CH3:8]>C1COCC1>[CH2:5]([C:9]1[N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[N:35]=[N:34][N:33]=3)=[CH:24][CH:25]=2)[C:17](=[O:56])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:57]([O:60][CH3:1])[CH2:58][CH3:59])[CH:15]=2)[N:10]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15233932HCID 15233932, compound

Product 1

HCID 20079354HCID 20079354, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.556 ml of methyl iodide in 5.0 ml of THF is added 0.071 g of 60% sodium hydride followed by 0.657 g of 2-butyl-6-(1-hydroxypropyl)-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]4(3H)-quinazolinone. The reaction is stirred for 16 hours at room temperature, then quenched with saturated NH4Cl solution and extracted with ether. The organics are dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 1:5 ethyl acetate/hexanes to provide 0.59 g of the desired product as a white solid. FAB MASS SPEC 751(M+H).

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionextracted with ether
  3. dry with materialThe organics are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography on silica gel
  7. washeluting with 1:5 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c2d9e651f5514f0aba64e92b93234dcf
Source dataset
uspto-grants-1994_03
Patent number
US05290780

Reaction notes

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