Tetrahydro-4H-pyran-4-ol → 7-Benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-one

HRID 1826288Notes

Reaction equation

HRID 1826288 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:43])[N:30](COC(=O)C(C)(C)C)[CH:31]=[N:32]2)=[C:27]([OH:44])[CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O[CH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>C(Cl)Cl>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:43])[NH:30][CH:31]=[N:32]2)=[C:27]([O:44][CH:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylateHCID 119746277-Benzyloxy-5-hydroxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 1358309117-Benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-oneYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Di-tert-butyl azodicarboxylate (16.3 g) was added portionwise to a stirred mixture of 7-benzyloxy-5-hydroxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (17 g), 4-hydroxytetrahydropyran (5.4 g) and methylene chloride (200 ml) that had been cooled to 5° C. The mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The mixture was evaporated and the residue was dissolved in a saturated methanolic ammonia solution. The resultant mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The solid so obtained was dried under vaccuum to give 7-benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-one (12.5 g); NMR Spectrum: (DMSOd6) 1.6–1.7 (m, 2H), 1.85–1.95 (m, 2H), 3.5 (m, 2H), 3.9 (m, 2H), 4.75 (m, 1H), 5.22 (s, 2H), 6.7 (d, 1H), 6.8 (d, 1H), 7.3–7.5 (m, 5H), 7.9 (s, 1H); Mass Spectrum: M+H+ 353.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe mixture was evaporated
  3. dissolutionthe residue was dissolved in a saturated methanolic ammonia solution
  4. stirringThe resultant mixture was stirred at ambient temperature for 16 hours
  5. customThe mixture was evaporated
  6. customthe residue was triturated under diethyl ether
  7. customThe solid so obtained
  8. customwas dried under vaccuum

Sources & evidence

ORD record
ord-785db5eefdad4038ab4585be386fbdae
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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