Ethanol → (s)-5-n-Octyl-2-[4-(6-methyloctyloxy)phenyl]-pyrimidine

HRID 4453Notes

Reaction equation

HRID 4453 reaction equation
[CH2:1]([C:9]1[C:10](Cl)=[N:11][C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C@@H:28]([CH3:31])[CH2:29][CH3:30])=[CH:18][CH:17]=2)=[N:13][C:14]=1Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O-2].[Mg+2].C(O)C>[C].[Pd].O>[CH2:1]([C:9]1[CH:14]=[N:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C@@H:28]([CH3:31])[CH2:29][CH3:30])=[CH:18][CH:17]=2)=[N:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 702EthanolHCID 6850729Magnesium monoxideHCID 54193042(s)-5-n-Octyl-2-[4-(6-methyloctyloxy)phenyl]-4,6-dichloro-pyrimidine

Product 1

HCID 18611652(s)-5-n-Octyl-2-[4-(6-methyloctyloxy)phenyl]-pyrimidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

Pour 1.88 g of optically active (s)-5-n-octyl-2-[4-(6-methyloctyloxy)phenyl]-4,6-dichloro-pyrimidine, 0.4 g of 10% palladium-carbon, 0.55 g of magnesium oxide, 60 ml of ethanol, and 45 ml of water, into a 200 ml flask, then add hydrogen under oil bath conditions at 50° C., until the logical amount of hydrogen has been absorbed. The catalyst is filtered and separated, then ether is extracted. After the ether layer is washed with water and with saturated salt water, and dried, the ether is evaporated. The resultant impure product is repeatedly refined, and 0.9 g of optically active (s)-5-n-octyl-2-[4-(6-methyloctyloxy)phenyl]-pyrimidine is obtained.

Workup

  1. custominto a 200 ml flask, then add hydrogen under oil bath conditions at 50° C., until the logical amount of hydrogen has been absorbed
  2. filtrationThe catalyst is filtered
  3. customseparated
  4. extractionether is extracted
  5. washAfter the ether layer is washed with water and with saturated salt water
  6. customdried
  7. customthe ether is evaporated

Sources & evidence

ORD record
ord-e62665853a104cb08a8caeb3781bea61
Source dataset
uspto-grants-1988_02
Patent number
US04725688

Reaction notes

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