Water → HCID 86681871, compound

HRID 1616077Notes

Reaction equation

HRID 1616077 reaction equation
[OH:1][C:2]1[C:3]2[O:10][CH:9]=[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.F[P-](F)(F)(F)(F)F.[N:31]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[N:32]1.N12CCCN=C1CCCCC2.O>O1CCCC1>[N:31]1([O:1][C:2]2[C:3]3[O:10][CH:9]=[C:8]([CH:11]4[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]4)[C:4]=3[N:5]=[CH:6][N:7]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[N:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724699PyBOPHCID 178451781HCID 178451781, compound

Product 1

HCID 86681871HCID 86681871, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, tert-butyl 4-(4-hydroxyfuro[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (1.06 g, 3.22 mmol) and 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (1.81 g, 3.49 mmol) were dissolved in anhydrous tetrahydrofuran (17 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (656 mg, 4.31 mmol) was added to the solution, and then the resultant solution was stirred at room temperature for 40 minutes. Water was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give tert-butyl 4-{4-[(1H-benzo[d][1,2,3]triazol-1-yl)oxy]furo[3,2-d]pyrimidin-7-yl}piperidine-1-carboxylate (1.19 g, 83%) as a white amorphous.

Workup

  1. customthe reaction liquid
  2. extractionwas extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2286a3eb521849c38ee792e150529f88
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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