1-Methylpiperazine → HCID 17974617, compound

HRID 1372984Notes

Reaction equation

HRID 1372984 reaction equation
[O:1]1[CH2:26][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:23])[N:10]([CH2:15][O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:24][CH3:25].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(Cl)(Cl)Cl>[OH:1][CH:2]([CH2:26][N:31]1[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]1)[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:23])[N:10]([CH2:15][O:16][C:17](=[O:22])[C:18]([CH3:20])([CH3:19])[CH3:21])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 21936045HCID 21936045, compound

Product 1

HCID 17974617HCID 17974617, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 7-(2,3-epoxypropoxy)-6-methoxy-3-(pivaloyloxymethyl)-3,4-dihydroquinazolin-4-one (5 g, 13.8 mmol) and N-methylpiperazine (1.7 ml) in chloroform (70 ml) was refluxed for 21 hours. After cooling the mixture was poured onto a column of silica and eluted with methanol/methylene chloride/ethylacetate (5/45/50) followed by (8/42/50) followed by methanol (saturated with ammonia)/ methylene chloride/methanol (5/45/50) followed by (8/42/50). The fractions containing the expected product were combined and the volatiles were removed under vacuum. The solid was triturated with ether, filtered, washed with ether and dried under vacuum to give 7-[2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy]-6-methoxy-3-(pivaloyloxymethyl)-3,4-dihydroquinazolin-4-one (4.8 g, 75%).

Workup

  1. temperatureAfter cooling the mixture
  2. additionwas poured onto a column of silica
  3. washeluted with methanol/methylene chloride/ethylacetate (5/45/50)
  4. additionThe fractions containing the expected product
  5. customthe volatiles were removed under vacuum
  6. customThe solid was triturated with ether
  7. filtrationfiltered
  8. washwashed with ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-1dc07a30337d48a18359218900135333
Source dataset
uspto-grants-2007_01
Patent number
US07160889B2

Reaction notes

Loading…