Ethanol → HCID 135966881, compound

HRID 1199305Notes

Reaction equation

HRID 1199305 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=3)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(N(CC)CC)C.C(O)C>[Pd].C(OCC)(=O)C>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([C:18]2[CH:19]=[N:20][C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[N:16][CH:17]=2)=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 14496412HCID 14496412, compound

Product 1

HCID 135966881HCID 135966881, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 120g of 2-(4-benzyloxyphenyl)-5-(4-butylpheny)pyrimidine, 13 g of palladium active carbon, 85 g of triethylamine, four liters of ethanol and one liter of ethyl acetate was stirred under a hydrogen atmosphere. After the palladium active carbon was removed and the solvent was distilled away, the residue was recrystallized by using a mixture of n-heptane and toluene, and 86 g of 5-(4-butylphenyl)-2-(4-hydroxylphenyl)pyrimidine was obtained. This compound showed melting points of 172.5°-173.3° C.

Workup

  1. customAfter the palladium active carbon was removed
  2. distillationthe solvent was distilled away
  3. customthe residue was recrystallized
  4. additiona mixture of n-heptane and toluene

Sources & evidence

ORD record
ord-e9f85a14eb1149feb52d796ce80374fe
Source dataset
uspto-grants-1990_02
Patent number
US04900472

Reaction notes

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