5-Benzyloxy-2-[4-(6-tetrahydropyranyloxy-1-heptynyl)phenyl]pyrimidine → 5-Hydroxy-2-[4-(6-tetrahydropyranyloxy1-heptyl)phenyl]pyrimidine

HRID 1956087Notes

Reaction equation

HRID 1956087 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][CH:26]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH3:27])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.[H][H]>[Pd].C1COCC1>[OH:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH3:27])=[CH:19][CH:20]=2)=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 223584285-Benzyloxy-2-[4-(6-tetrahydropyranyloxy-1-heptynyl)phenyl]pyrimidineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 223584305-Hydroxy-2-[4-(6-tetrahydropyranyloxy1-heptyl)phenyl]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a reactor equipped with a stirrer and a thermometer, 5-benzyloxy-2-[4-(6-tetrahydropyranyloxy-1-heptynyl)phenyl]pyrimidine, 5% Pd/C and THF are charged. After replacing an internal atmosphere of the reactor by hydrogen gas under atmospheric pressure, the mixture is reacted at room temperature for 10 hours in a hydrogen atmosphere under ordinary pressure. After filtrating the catalyst off, the reaction mixture is evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography to obtain 5-hydroxy-2-[4-(6-tetrahydropyranyloxy1-heptyl)phenyl]pyrimidine.

Workup

  1. customIn a reactor equipped with a stirrer
  2. filtrationAfter filtrating the catalyst off, the reaction mixture
  3. customis evaporated under reduced pressure
  4. customA resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c10bd8bdaa749ddaab1013b9407da2b
Source dataset
uspto-grants-1998_07
Patent number
US05779934

Reaction notes

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