Cesium carbonate → 2,6-dihydro-2-methyl-4-(2-methylpropyl)-6-[3,4,5-trimethoxyphenyl]methyl-1H-pyrrolo[3,4-d]pyridazin-1-one

HRID 1835149Notes

Reaction equation

HRID 1835149 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][NH:10][CH:11]=[C:5]2[C:4]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:3]1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH2:21]Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.Cl>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:21][C:20]3[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:19]=3)[CH:11]=[C:5]2[C:4]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:3]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 1355247842-methyl-4-(2-methylpropyl)-1H,2H,6H-pyrrolo[3,4-d]pyridazin-1-one

Product 1

HCID 235032722,6-dihydro-2-methyl-4-(2-methylpropyl)-6-[3,4,5-trimethoxyphenyl]methyl-1H-pyrrolo[3,4-d]pyridazin-1-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-dihydro-2-methyl-4(2-methylpropyl)-1H-pyrrolo[3,4-d]pyridazin-1-one (Example 18 step a, 0.031 g), 3,4,5-trimethoxybenzyl chloride (0.038 g), and cesium carbonate (0.090 g) in dry dimethyl formamide (0.8 ml) was stirred for 16 hours, and then diluted with dilute hydrochloric acid. The mixture was extracted with ethyl acetate, which was washed with brine, dried, and evaporated to a solid. The solid was purified by chromatography on silica (dichloromethane/ethanol 9:1) to give 2,6-dihydro-2-methyl-4-(2-methylpropyl)-6-[3,4,5-trimethoxyphenyl]methyl-1H-pyrrolo[3,4-d]pyridazin-1-one (0.033 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate, which
  2. washwas washed with brine
  3. customdried
  4. customevaporated to a solid
  5. customThe solid was purified by chromatography on silica (dichloromethane/ethanol 9:1)

Sources & evidence

ORD record
ord-b61d3c651350422fbcff31dd2e27ea09
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

Loading…