Triethylamine → 2-((6-((2,5-Dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)oxy)ethanol

HRID 1053927Notes

Reaction equation

HRID 1053927 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]([O:19][CH2:20][CH2:21][OH:22])[CH:14]2[O:13][CH2:12]1.C(N(CC)CC)C>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH:11]2[CH:15]3[O:16][CH2:17][CH:18]([O:19][CH2:20][CH2:21][OH:22])[CH:14]3[O:13][CH2:12]2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 1183879542-((6-Aminohexahydrofuro[3,2-b]furan-3-yl)oxy)ethanol

Product 1

HCID 1183879932-((6-((2,5-Dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)oxy)ethanolYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2,4,5-trichloropyrimidine (0.71 g, 3.88 mmol) in EtOH (20 mL) were added 2-((6-aminohexahydrofuro[3,2-b]furan-3-yl)oxy)ethanol (crude product) and N,N-diethylethanamine (1.10 mL, 7.89 mmol). The mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified by silica chromatography (DCM/MeOH (v/v)=50/1) to give the title compound as brown liquid (0.21 g, 16%, for three steps).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica chromatography (DCM/MeOH (v/v)=50/1)

Sources & evidence

ORD record
ord-0267adca91bf4b0387b1fb03ac2f1c0c
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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