2-{4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]-1-piperazinyl}-5-benzyloxypyrimidine → 2-{4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]-1-piperazinyl}-5-hydroxypyrimidine

HRID 1757062Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([CH3:32])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([O:24]CC4C=CC=CC=4)=[CH:20][N:19]=3)[CH2:14][CH2:13]2)[C:6]=1[Cl:7]>[Pd].CO>[Cl:1][C:2]1[N:3]=[C:4]([CH3:32])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][N:15]([C:18]3[N:23]=[CH:22][C:21]([OH:24])=[CH:20][N:19]=3)[CH2:16][CH2:17]2)[C:6]=1[Cl:7]

Participants

Conditions

Temperature: 24 °C

Procedure

A mixture of 2.90 g (6.10 mmol) of 2-{4-[4-(4,5-dichloro-2-methylimidazol-1-yl )butyl]-1-piperazinyl}-5-benzyloxypyrimidine and 0.30 g of 10% palladium on carbon in 50 ml of methanol is stirred for 12 hours under a hydrogen atmosphere at room temperature (24° C.) and at a pressure of 0.28 MPa. After filtration, washing with methanol and evaporation to dryness, the product is chromatographed on silica gel, yielding 1.39 g (59%) of 2-{4-[4-(4,5-dichloro-2-methylimidazol -1-yl)butyl]-1-piperazinyl}-5-hydroxypyrimidine with a melting point of 154°-6° C.

Workup

filtrationAfter filtration
washwashing with methanol and evaporation to dryness
customthe product is chromatographed on silica gel

Sources & evidence

ORD record: ord-4c20446dcdc4416489fc29654b713d14
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05444059

Reaction notes

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