Sodium hydride → HCID 131718091, compound

HRID 2255539Notes

Reaction equation

HRID 2255539 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]([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:21]1([C:27]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:28]2[C:32]([C:33]3[C:38]([C:39]4[CH:44]=[CH:43][C:42]([CH2:45]Br)=[CH:41][CH:40]=4)=[CH:37][CH:36]=[C:35]([F:47])[CH:34]=3)=[N:31][N:30]=[N:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:1]([C:5]1[N:14]([CH2:45][C:42]2[CH:41]=[CH:40][C:39]([C:38]3[CH:37]=[CH:36][C:35]([F:47])=[CH:34][C:33]=3[C:32]3[N:28]([C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[N:29]=[N:30][N:31]=3)=[CH:44][CH:43]=2)[C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:16]([CH3:17])[CH3:18])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 131718089HCID 131718089, compoundHCID 178441841HCID 178441841, compound

Product 1

HCID 131718091HCID 131718091, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-butyl-6-isopropylquinazolinone (55.6 mg; 0.228 mmol) (Example 8) in dry DMF (1.5 mL) was added NaH, 80% oil dispersion, (11.8 mg; 1.5 eq). The reaction mixture was allowed to stir for 30 min. under N2. To this was added a solution of N-triphenylmethyl-5-(4-fluoro-4'-bromomethyl-biphen-2-yl)tetrazole (crude) in dry DMF (1.5 mL). The reaction was stirred under N2 for 3 hrs. then quenched with saturated NH4Cl solution. The solvent was removed at high vacuum, replaced by EtOAc, and the insoluable salts filtered off. The product was purified by flash chromatography on a silica column eluting with Hex/EtOAc (35:1) to afford 94.5 mg (56%) of the titled compound. Characteristic peaks 1H-NMR (300 MHz, CDCl3) δ 0.87 (t, 3H), 1.30 (d, 6H), 1.68 (m, 2H), 2.63 (t, 2H), 3.05 (q, 1H), 5.28 (s, 2H), 8.13 (s, 1H).

Workup

  1. stirringThe reaction was stirred under N2 for 3 hrs
  2. customthen quenched with saturated NH4Cl solution
  3. customThe solvent was removed at high vacuum
  4. filtrationthe insoluable salts filtered off
  5. customThe product was purified by flash chromatography on a silica column
  6. washeluting with Hex/EtOAc (35:1)

Sources & evidence

ORD record
ord-afe4347e26494510a3e037d9fc66ce1e
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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