Diisobutylaluminum hydride → HCID 136205555, compound

HRID 1489032Notes

Reaction equation

HRID 1489032 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:24](=[O:25])[N:15]3[CH2:16][NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:14]3=[N:13]2)=[CH:8][CH:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[OH:3][CH2:4][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:24](=[O:25])[N:15]3[CH2:16][NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:14]3=[N:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 136024933HCID 136024933, compound2×

Product 1

HCID 136205555HCID 136205555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-[4-(Ethoxycarbonyl)phenyl]-5,6-dihydro-1,2,4-triazolo-[4,3-c]-quinazolin-3-one (Compound 18) (1 g, 3.0 mmol) was mixed with THF at 0° C. DIBAL (1.5M in Toluene, 4.6 ml) was added to the reaction dropwise and stirred for 10 min. at 0° C. The reaction was quenched with 10% NaOH solution and extracted with CH2Cl2 (3×100 ml). The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure to afford 2-[4-(hydroxymethyl)-phenyl]-5,6-dihydro-1,2,4-triazolo[4,3-c]-quinazolin-3-one (Compound 19), m.p. 152°-154° C.

Workup

  1. customThe reaction was quenched with 10% NaOH solution
  2. extractionextracted with CH2Cl2 (3×100 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-206cce6bb25a4660a964845cbcb5379f
Source dataset
uspto-grants-1997_10
Patent number
US05677309

Reaction notes

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