Triethylamine → 6-((2,5-Dichloropyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[CH3:10][NH:11][CH:12]1[CH:16]2[O:17][CH2:18][CH:19]([OH:20])[CH:15]2[O:14][CH2:13]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:11]([CH3:10])[CH:12]2[CH:16]3[O:17][CH2:18][CH:19]([OH:20])[CH:15]3[O:14][CH2:13]2)[C:5]([Cl:9])=[CH:4][N:3]=1Participants
5
Procedure
To a solution of 2,4,5-trichloropyrimidine (484.9 mg, 2.64 mmol) and 6-(methylamino)hexahydrofuro[3,2-b]furan-3-ol (530.2 mg, 3.33 mmol) in EtOH (30 mL) was added Et3N (566.0 mg, 5.59 mmol). After addition, the reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was dissolved in a mixture of EtOAc and water (1/1 (v/v), 100 mL) and extracted with EtOAc (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2) to give the title compound as a pale yellow solid (760.2 mg, 94.0%).
Workup
- additionAfter addition
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in a mixture of EtOAc and water (1/1 (v/v), 100 mL)
- extractionextracted with EtOAc (100 mL×3)
- washThe combined organic phases were washed with brine (100 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2)
Sources & evidence
- ORD record
- ord-dea2b58980e94f07865767467da62f8d
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394281B2
Reaction notes
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