Ethanol → 2-(4-Hydroxyphenyl)-5-pyrimidinol

HRID 1608901Notes

Reaction equation

HRID 1608901 reaction equation
Cl([O-])(=O)(=O)=O.Cl.[OH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[NH:13])=[CH:10][CH:9]=1.[CH3:17][O-].[Na+].[CH2:20]([OH:22])[CH3:21]>CO.O.C(O)(=O)C>[OH:22][C:20]1[CH:17]=[N:13][C:12]([C:11]2[CH:15]=[CH:16][C:8]([OH:7])=[CH:9][CH:10]=2)=[N:14][CH:21]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 123351PerchlorateHCID 217124Benzenecarboximidamide, 4-hydroxy-, hydrochloride (1:1)HCID 10942334Sodium Methoxide

Product 1

HCID 40491572-(4-Hydroxyphenyl)-5-pyrimidinol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a one-liter flask, 30 g (0.09 moles) of 2benzyloxytrimethinium perchlorate (prepared essentially according to the procedure of A. Holy and Z. Arnold, Collection Czechoslov. Chem. Commun. 38, 1372 (1973)), 15.6 g (0.09 moles) of p-hydroxybenzamidine hydrochloride, 82.5 ml (0.36 moles) of 25% sodium methoxide in methanol, and 500 ml of ethanol were combined. The resulting mixture was heated to reflux overnight, and then cooled to room temperature. Then, 75 ml of glacial acetic acid and 300 ml of deionized water was added to the flask, resulting in precipitation of the product. The product was collected by filtration, washed with water, and air dried. The yield of 5-benzyloxy-2-(4-hydroxyphenyl)pyrimidine was 23.06 g (92%). This material was then hydrogenated on a Parr Hydrogenator with catalytic 10% palladium on carbon in tetrahydrofuran under 413.7 kPa hydrogen pressure for about 18 hours. When the hydrogenation was complete, the catalyst was removed by filtration, and the solvent was removed on a rotary evaporator to yield 5-hydroxy-2-(4-hydroxyphenyl)pyrimidine. The final product, 5-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)-2-(4hydroxyphenyl)pyrimidine, was prepared from 5-hydroxy-2-(4-hydroxyphenyl)pyrimidine and 5-butoxy-2,2,3,3,4,4hexafluoropentyltrifluoromethanesulfonate (prepared essentially as in Example 2) essentially as described in Example 6.

Workup

  1. customArnold, Collection Czechoslov
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux overnight
  4. customresulting in precipitation of the product
  5. filtrationThe product was collected by filtration
  6. washwashed with water, and air
  7. customdried
  8. customthe catalyst was removed by filtration
  9. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-e11dcc5c25c841e39627505c7cbb4dde
Source dataset
uspto-grants-1995_03
Patent number
US05399291

Reaction notes

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