Triphenylphosphine → 7-methoxy-5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4(3H)-one

HRID 631351Notes

Reaction equation

HRID 631351 reaction equation
C(OC[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([O:21][CH3:22])=[CH:15][C:16]=2[OH:20])[N:11]=[CH:10]1)(=O)C(C)(C)C.[O:23]1[CH2:28][CH2:27][CH:26](O)[CH2:25][CH2:24]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C(Cl)Cl>[CH3:22][O:21][C:14]1[CH:13]=[C:12]2[C:17]([C:18](=[O:19])[NH:9][CH:10]=[N:11]2)=[C:16]([O:20][CH:26]2[CH2:27][CH2:28][O:23][CH2:24][CH2:25]2)[CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylateHCID 119745575-Hydroxy-7-methoxy-3-pivaloyloxymethyl-quinazolin-4-one

Product 1

HCID 1355106967-methoxy-5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4(3H)-oneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-hydroxy-7-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate (2.50 g, 8.16 mmol), tetrahydro-4H-pyran-4-ol (1.02 g, 10 mmol), and Ph3P (3.41 g, 13 mmol) in CH2Cl2 (40 mL) at 0° C. was added di t-butyl azodicarboxylate (3.993 g, 13 mmol). It was stirred at room temperature for 2 hour. After solvent was evaporated under reduced pressure, to the residue was added 7 N NH3/MeOH (80 mL) and stirred at room temperature overnight. A solid was precipitated. It was filtered, washed with MeOH, and dried under vacuum to afford 7-methoxy-5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4(3H)-one as solid (1.091 g, 76%). 1H NMR (300 MHz, DMSO-d6) δ 10.6 (br, 1H), 7.98 (s, 1H), 6.74 (d, 1H), 6.69 (d, 1H), 4.79 (m, 1H), 3.97 (m, 2H), 3.91 (s, 3H), 3.57 (m, 2H), 1.98 (m, 2H), 1.74 (m, 2H); LC-MS (ESI) m/z 277 (M+H)+.

Workup

  1. customAfter solvent was evaporated under reduced pressure, to the residue
  2. additionwas added 7 N NH3/MeOH (80 mL)
  3. stirringstirred at room temperature overnight
  4. customA solid was precipitated
  5. filtrationIt was filtered
  6. washwashed with MeOH
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d85185c0c55a41218bac08832929efd9
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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