1-Methylpiperazine → 6-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 454237Notes

Reaction equation

HRID 454237 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:24])[N:11]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:25][CH3:26].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[C:14]3[C:9]([C:10](=[O:24])[N:11]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[N:13]3)=[CH:8][C:7]=2[O:25][CH3:26])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 218748177-(3-Bromopropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 220306066-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 83%

Conditions

Temperature
100 °C

Procedure

A suspension of 7-(3-bromopropoxy)-6-methoxy-3-((pivaloyloxy)methyl) -3,4-dihydroquinazolin-4-one (36.7 g, 86 mmol) in 1-methylpiperazine (370 ml) was stirred at 100° C. for 90 minutes. After removal of the volatiles under vacuum, the residue was partitioned between methylene chloride and aqueous ammonium chloride. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The solid was triturated with ether, filtered, washed with ether and dried under vacuum to give 7-(3-(4-methylpiperazin-1-yl)propoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (31.9 gr, 83%).

Workup

  1. customAfter removal of the volatiles under vacuum
  2. customthe residue was partitioned between methylene chloride and aqueous ammonium chloride
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe solid was triturated with ether
  8. filtrationfiltered
  9. washwashed with ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-96637d845e334c469fa286d526c39481
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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