Sodium hydride → HCID 70108448, compound

HRID 1938523Notes

Reaction equation

HRID 1938523 reaction equation
[H-].[Na+].[CH:3]([C:5]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:26])[CH:11]=2)[N:6]=1)=O.[CH3:27][CH2:28][O:29][C:30]([CH:32](P(OCC)(OCC)=O)[CH3:33])=[O:31].Cl.C(O)C>O1CCCC1>[CH2:28]([O:29][C:30](/[C:32](/[CH3:33])=[CH:3]/[C:5]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:26])[CH:11]=2)[N:6]=1)=[O:31])[CH3:27]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 18796731HCID 18796731, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 70108448HCID 70108448, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.52 g (0.013 mol) of sodium hydride was added to a solution of 4.00 g (0.0117 mol) of 2-formyl-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline in 250 ml of tetrahydrofuran. 2.8 ml (0.013 mol) of triethyl 2-phosphonopropionate was dropped into the mixture prepared above under stirring and cooling with ice. The mixture thus prepared was stirred under cooling with ice for a while, heated to room temperature and stirred for additional one hour, followed by the addition of 1.5 ml of 8M hydrochloric acid/ethanol. The obtained mixture was passed through a small amount of silica gel and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) and recrystallized from chloroform/n-hexane to give 2.00 g of the title compound.

Workup

  1. customprepared above
  2. temperaturecooling with ice
  3. customThe mixture thus prepared
  4. stirringwas stirred
  5. temperatureunder cooling with ice for a while
  6. stirringstirred for additional one hour
  7. distillationdistilled under a reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)
  10. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-115bad16517141dbb841ef62641ac325
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Reaction notes

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