Carbon Dioxide → HCID 21912243, compound

HRID 1831696Notes

Reaction equation

HRID 1831696 reaction equation
[Li]CCCC.Br[C:7]1[C:8]([NH:20][C:21]2[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[CH3:29])=[N:9][C:10]([CH3:19])=[N:11][C:12]=1[O:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16].[C:30](=[O:32])=[O:31]>C1COCC1>[CH2:15]([CH:14]([O:13][C:12]1[C:7]([C:30]([OH:32])=[O:31])=[C:8]([NH:20][C:21]2[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[CH3:29])[N:9]=[C:10]([CH3:19])[N:11]=1)[CH2:17][CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 21912385HCID 21912385, compoundHCID 178418339Butyllithium

Product 1

HCID 21912243HCID 21912243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of n-BuLi in THF was added a solution of [5-bromo-6-(1-ethyl-propoxy)-2-methyl-pyrimidin-4-yl]-(2,4,6-trimethyl-phenyl)-amine in THF at −78° C. After stirring for 10 minutes, CO2(g) was added at −78° C. and stirred at that temperature for 1 hour, then gradually warmed to room temperature. The resulting mixture was quenched with water and adjusted to pH 2 to 3 and extracted with chloroform. The organic layer was separated, dried and concentrated to dryness. The residue was purified through silica gel column chromatography to give the title compound as a solid, mp. 118–120° C., Anal. For C20H27N3O3 calc.: C, 67.20; H, 7.61; N, 11.76; found: C, 67.25; H, 7.87; N, 11.48.

Workup

  1. stirringstirred at that temperature for 1 hour
  2. customThe resulting mixture was quenched with water
  3. extractionextracted with chloroform
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-fcd269743715489191e08872ddbdc7a1
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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