Triethylamine → 6((2-Chloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-ol

HRID 1053921Notes

Reaction equation

HRID 1053921 reaction equation
Cl.[NH2:2][CH:3]1[CH:7]2[O:8][CH2:9][CH:10]([OH:11])[CH:6]2[O:5][CH2:4]1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1.CCN(CC)CC>CCO>[Cl:12][C:13]1[N:18]=[C:17]([NH:2][CH:3]2[CH:7]3[O:8][CH2:9][CH:10]([OH:11])[CH:6]3[O:5][CH2:4]2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 1183879596-Aminohexahydrofuro[3,2-b]furan-3-ol hydrochloride

Product 1

HCID 1183879696((2-Chloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-olYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6-aminohexahydrofuro[3,2-b]furan-3-ol hydrochloride (363 mg, 2.0 mmol) in EtOH (10 mL) were added 2,4-dichloropyrimidine (298 mg, 2.0 mmol) and Et3N (1.01 g, 10.0 mmol) and the mixture was stirred at rt under nitrogen atmosphere overnight. The reaction mixture was filtered and washed with DCM (30 mL) and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (DCM/MeOH=30/1) to give the title compound as a white solid (165 mg, 32%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DCM (30 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (DCM/MeOH=30/1)

Sources & evidence

ORD record
ord-43d7321e42e74c23bf96c9e329b700d1
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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