Tetrahydrofuran → 6-(aminomethyl)-2-phenylquinazolin-4(3H)-one

HRID 923631Notes

Reaction equation

HRID 923631 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:3]1.C1COCC1.[BH4-].[Na+]>CO.O.[Co](Cl)Cl>[NH2:13][CH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:3][C:2]2=[O:1]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 136636244HCID 136636244, compound

Product 1

HCID 1366362456-(aminomethyl)-2-phenylquinazolin-4(3H)-oneYield 56%

Reagents, catalysts & solvents 2

HCID 16211468Cobalt(II) chloride hydrateCatalystHCID 887MethanolSolvent

Procedure

Prepared from INT-87. To a stirring solution of 4-oxo-2-phenyl-3,4-dihydroquinazoline-6-carbonitrile INT-87 (540 mg, 2.18 mmol) in MeOH (30 mL) and THF (10 mL) was added cobalt(II) chloride hydrate (646 mg, 4.37 mmol) and sodium borohydride (826 mg, 21.8 mmol) portionwise. After stirring at room temperature for 30 min the reaction mixture was quenched with 1 M HCl (5 mL) and filtered through a celite plug, washing with THF (50 mL). The mixture was diluted with EA (100 mL) and washed with NaHCO3 (120 mL) and brine (20 mL). The organics were dried over MgSO4 and concentrated in vacuo to afford 306 mg (56%) of 6-(aminomethyl)-2-phenylquinazolin-4(3H)-one INT-88 as a white powder. LCMS-ESI (m/z) calculated for C15H13N3O: 251; found 250 [M−H]−, tR=0.80 min (Method 10).

Workup

  1. customPrepared from INT-87
  2. customwas quenched with 1 M HCl (5 mL)
  3. filtrationfiltered through a celite plug
  4. washwashing with THF (50 mL)
  5. additionThe mixture was diluted with EA (100 mL)
  6. washwashed with NaHCO3 (120 mL) and brine (20 mL)
  7. dry with materialThe organics were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12005e7f5b394d0f9d04a208106f351f
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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