Dimedone → 3-Acetylamino-5-[(4,6-dimethoxypyrimidin-2yl)oxy]-2-methylindol-4-carboxylic Acid

HRID 52015

Reaction equation

HRID 52015 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:12]([C:14]([O:16]CC=C)=[O:15])=[C:11]([O:20][C:21]3[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=3)[CH:10]=[CH:9][C:8]=2[NH:7][C:6]=1[CH3:31])(=[O:3])[CH3:2].CC1(C)CC(=O)CC(=O)C1>O1CCCC1>[C:1]([NH:4][C:5]1[C:13]2[C:12]([C:14]([OH:16])=[O:15])=[C:11]([O:20][C:21]3[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=3)[CH:10]=[CH:9][C:8]=2[NH:7][C:6]=1[CH3:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31358DimedoneHCID 19962751Allyl 3-Acetylamino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate

Product 1

HCID 199627543-Acetylamino-5-[(4,6-dimethoxypyrimidin-2yl)oxy]-2-methylindol-4-carboxylic AcidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.49 g of allyl 3-acetylamino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of tetrahydrofuran, and 0.1 g of dimedone and 0.01 g of tetrakistriphenylphosphine palladium were added thereto. The mixture was stirred at room temperature for 4 hours. Crystals obtained by concentration under reduced pressure, was washed with isopropyl ether to obtain 0.41 g (yield: 93%) of the desired compound. mp: 230°-233° C.

Workup

  1. customCrystals obtained by concentration under reduced pressure
  2. washwas washed with isopropyl ether

Sources & evidence

ORD record
ord-d8978749e11948fcb45208fd1bc39b1f
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Linked notes

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