3-benzyl-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one → 6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one

HRID 386597Notes

Reaction equation

HRID 386597 reaction equation
C([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([O:30][CH3:31])=[C:14]([O:19][CH:20]3[CH2:29][CH2:28][C:23]4([O:27][CH2:26][CH2:25][O:24]4)[CH2:22][CH2:21]3)[CH:15]=2)[N:10]=[CH:9]1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[O:18]=[C:17]1[C:16]2[C:11](=[CH:12][C:13]([O:30][CH3:31])=[C:14]([O:19][CH:20]3[CH2:21][CH2:22][C:23]4([O:24][CH2:25][CH2:26][O:27]4)[CH2:28][CH2:29]3)[CH:15]=2)[N:10]=[CH:9][NH:8]1

Participants

5

Reactant 2

HCID 581572543-benzyl-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1359917776-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

16.0 g 3-benzyl-3,4-dihydro-4-oxo-6-(1,4-dioxa-spiro[4.5]decan-8-yl-oxy)-7-methoxy-quinazoline in 150 ml glacial acetic acid are hydrogenated in the presence of 1.6 g palladium on activated charcoal (10% Pd) at 60° C. at a hydrogen pressure of 50 psi. The catalyst is filtered off and the filtrate is evaporated down, combined with toluene and evaporated down again. The residue is mixed with water and made slightly alkaline with saturated sodium hydrogen carbonate solution. The precipitate is suction filtered and dried.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated down
  3. customevaporated down again
  4. additionThe residue is mixed with water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-93f80497f2994c70ad56fe7829f42652
Source dataset
uspto-grants-2013_02
Patent number
US08372855B2

Reaction notes

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