Triethylamine → HCID 86627796, compound

HRID 645506Notes

Reaction equation

HRID 645506 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:8](Cl)=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3].CCN(CC)CC.[CH3:22][NH:23][CH2:24][CH:25]1[CH2:32][CH2:31][C:28]2([CH2:30][CH2:29]2)[CH2:27][CH2:26]1>O1CCOCC1>[CH2:1]([O:4][C:5]([C:7]1[C:8]([N:23]([CH3:22])[CH2:24][CH:25]2[CH2:32][CH2:31][C:28]3([CH2:29][CH2:30]3)[CH2:27][CH2:26]2)=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22766293HCID 22766293, compoundHCID 57580370N-Methylspiro[2.5]octane-6-methanamine

Product 1

HCID 86627796HCID 86627796, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of the 2,4-dichloropyrimidine-5-carboxylic acid allyl ester (1.6 mmol) in dioxane (6 mL) is added Et3N (2.4 mmol) at room temperature. A solution of methyl-spiro[2.5]oct-6-ylmethylamine (1.6 mmol) in dioxane (2.0 mL) is added dropwise to the reaction mixture. The reaction mixture is stirred at room temperature for 12 h and the reaction is quenched by the addition of water. The mixture is extracted with CH2Cl2. The organic extracts are dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified by silica gel column chromatography to give the title compound (370 mg); 1H NMR (CDCl3) δ 0.15-0.19 (m, 2H), 0.25-0.29 (m, 2H), 0.87-0.91 (m, 2H), 1.08-1.20 (m, 2H), 1.60-1.85 (m, 5H), 2.95 (s, 3H), 3.59 (d, 2H), 4.77-4.78 (m, 2H), 5.29-6.08 (m, 1H), 8.48 (s, 1H).

Workup

  1. customthe reaction is quenched by the addition of water
  2. extractionThe mixture is extracted with CH2Cl2
  3. dry with materialThe organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-17fba5c7bc2b4133b000885c342ed794
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

Loading…