4-Cyanopiperidine → 1-(2-Chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbonitrile

HRID 1038845

Reaction equation

HRID 1038845 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]#[N:19])[CH2:14][CH2:13]1>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]#[N:19])[CH2:14][CH2:13]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 1382234-CyanopiperidineHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidine

Product 1

HCID 866651101-(2-Chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbonitrileYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,4-dichlorofuro[3,2-d]pyrimidine (0.40 g, 2.1 mmol, ArkPharm), piperidine-4-carbonitrile (0.23 g, 2.1 mmol, Oakwood) and TEA (0.59 mL, 4.2 mmol) in 1,4-dioxane (10 mL) was stirred at about 25° C. for about 12 h. The solvent was removed under reduced pressure and water (5 mL) and DCM (10 mL) were added to the residue. The layers were separated and the organic solution was concentrated under reduced pressure to give 1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbonitrile (0.50 g, 90%): LC/MS (Table 2, Method 1) Rt=0.76 min; MS m/z: 263 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure and water (5 mL) and DCM (10 mL)
  2. additionwere added to the residue
  3. customThe layers were separated
  4. concentrationthe organic solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1b6dfa90d5b464cab405f3abfa1d06a
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Linked notes

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