HCID 58553807, compound → HCID 58553813, compound

HRID 1182814Notes

Reaction equation

HRID 1182814 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]([N:15]2[C:20](=[O:21])[C:19]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)=[C:18]([CH2:37][CH2:38][CH2:39][CH3:40])[N:17]=[C:16]2[CH3:41])=[N:13][CH:14]=1)C1C=CC=CC=1>[Pd].CO>[CH2:37]([C:18]1[N:17]=[C:16]([CH3:41])[N:15]([C:12]2[N:13]=[CH:14][C:9]([OH:8])=[CH:10][N:11]=2)[C:20](=[O:21])[C:19]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:27][CH:28]=1)[CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 1

HCID 58553807HCID 58553807, compound

Product 1

HCID 58553813HCID 58553813, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the methanol (10 mL) solution of 4′-{[1-[5-(benzyloxy)pyrimidin-2-yl]-4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (235 mg, 0.434 mmol), 10% Pd—C (containing 50% moisture, 120 mg) was added for hydrogenation. After stirring at room temperature for 1 hr, the reaction mixture was filtered through a pad of celite and washed with methanol. The filtrate was distilled off and the resulting residues were subjected to silica gel column chromatography (chloroform:methanol=10:1) to obtain 4′-{[4-butyl-1-(5-hydroxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. washwashed with methanol
  3. distillationThe filtrate was distilled off

Sources & evidence

ORD record
ord-c3fb0da0c1514a7b9cd794d22df8ead8
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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