Ammonia → HCID 135510689, compound

HRID 641744

Reaction equation

HRID 641744 reaction equation
N(C(OC(C)(C)C)=O)=NC([O-])=O.[OH:13][C:14]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:15]=1[C:16](=[O:34])[N:17](COC(=O)C(C)(C)C)[CH:18]=[N:19]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:55]1[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]1.N>C(Cl)Cl>[CH3:25][O:24][C:23]1[C:14]([O:13][CH:55]2[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]2)=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][NH:17][C:16]2=[O:34]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 11974824HCID 11974824, compoundHCID 86609045Tert-butyl azodicarboxylate

Product 1

HCID 135510689HCID 135510689, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of di-(tert-butyl azodicarboxylate (1.75 g) in methylene chloride (3 ml) was added to a stirred mixture of 5-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (1.55 g), triphenylphosphine (1.99 g), 4-hydroxy-1-methylpiperidine (0.75 g) and methylene chloride (12 ml) which had been cooled to 5° C. The mixture was stirred at ambient temperature for 1 hour. The mixture was evaporated and the residue was purified by column chromatography on silica using a 9:10:1 mixture of methylene chloride, ethyl acetate and a saturated methanolic ammonia solution as eluent. The material so obtained was stirred in a saturated methanolic ammonia solution for 48 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The resultant solid was washed with diethyl ether and dried under vacuum to give 6-methoxy-5-(N-methylpiperidin-4-yloxy)-3,4-dihydroquinazolin-4-one (0.92 g); NMR Spectrum: (DMSOd6) 1.7-1.9 (m, 4H), 1.95 (t, 2H), 2.15 (s, 3H), 2.7 (m, 2H), 3.85 (s, 3H), 4.08 (m, 1H), 7.4 (d, 1H), 7.6 (d, 1H), 7.85 (s, 1H), 11.8 (br s, 1H); Mass Spectrum: M+H+ 290.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. additiona 9:10:1 mixture of methylene chloride, ethyl acetate
  4. customThe material so obtained
  5. customThe mixture was evaporated
  6. customthe residue was triturated under diethyl ether
  7. washThe resultant solid was washed with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-26a785309f7744ef9183820051903752
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Linked notes

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