HCID 57714115, compound → HCID 57714122, compound

HRID 1163030Notes

Reaction equation

HRID 1163030 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[CH:21])=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1>CCO.[Pd]>[CH3:1][C:2]([CH3:22])([CH3:23])[CH2:3][N:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH3:21])=[CH:18][CH:19]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1

Participants

4

Reactant 1

HCID 57714115HCID 57714115, compound

Product 1

HCID 57714122HCID 57714122, compoundYield 112%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[(2,2-Dimethyl-propyl)-(4-ethynyl-benzyl)-amino]-pyrimidine-2-carbonitrile (47 mg, 0.11 mmoles) is dissolved in 5 ml of EtOH and 10% Pd—C (5 mg) is added at rt. The mixture is stirred under hydrogen at rt for overnight and is filtered through a pad of Celite which is washed with EtOH. The filtrate is concentrated and the crude product is purified by silica gel column chromatography to give 38 mg of desired 4-[(2,2-dimethyl-propyl)-(4-ethyl-benzyl)-amino]-pyrimidine-2-carbonitrile in 77% yield.

Workup

  1. filtrationis filtered through a pad of Celite which
  2. washis washed with EtOH
  3. concentrationThe filtrate is concentrated
  4. customthe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7eba47d717740a1a29999279891b557
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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