2,4,5-Trichloropyrimidine → 2-(6-((2,5-Dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl) isoindoline-1,3-dione

HRID 1053942Notes

Reaction equation

HRID 1053942 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][CH:11]1[CH:15]2[O:16][CH2:17][CH:18]([N:19]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])[CH:14]2[O:13][CH2:12]1>CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH:11]2[CH:15]3[O:16][CH2:17][CH:18]([N:19]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]4=[O:29])[CH:14]3[O:13][CH2:12]2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2372592,4,5-TrichloropyrimidineHCID 1183879492-(6-Aminohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

Product 1

HCID 1183879632-(6-((2,5-Dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl) isoindoline-1,3-dioneYield 13.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4,5-trichloropyrimidine (1.45 g, 7.9 mmol) in MeOH (40 mL) were added triethanamine (970 mg, 9.6 mmol) and 2-(6-aminohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione (crude product from above step). The mixture was stirred at room temperature overnight, Then concentrated in vacuo, the residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/3) to give the desired compound as a white solid (450 mg, 13.5% three steps).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/3)

Sources & evidence

ORD record
ord-1a952bd582db49aa92d9ca8de13d298b
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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