{4-[5-(3-Amino-3-methyl-but-1-ynyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine → {4-[5-(3-Amino-3-methyl-butyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HRID 1434952Notes

Reaction equation

HRID 1434952 reaction equation
[NH2:1][C:2]([CH3:28])([CH3:27])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][C:21]([CH3:24])([CH3:23])[NH:20][C:19]([CH3:26])([CH3:25])[CH2:18]3)[N:11]=2)=[CH:7][CH:6]=1>CO.[Pd]>[NH2:1][C:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][C:21]([CH3:24])([CH3:23])[NH:20][C:19]([CH3:26])([CH3:25])[CH2:18]3)[N:11]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 11211671{4-[5-(3-Amino-3-methyl-but-1-ynyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

Product 1

HCID 11373006{4-[5-(3-Amino-3-methyl-butyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

{4-[5-(3-Amino-3-methyl-but-1-ynyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (Example 5, 100 mg, 0.252 mmol) in MeOH (100 ml) was hydrogenated over Pd/C (10%, 50 mg) at 1 atm for 2 hours. The reaction mixture was filtered, evaporated to dryness and purified via chromatography on silicagel (DCM/MeOH/ammonia: 95/5/1 to 90/10/1) to give the title compound as colorless solid, which crystallized from ether.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. custompurified via chromatography on silicagel (DCM/MeOH/ammonia: 95/5/1 to 90/10/1)

Sources & evidence

ORD record
ord-0f6d35b88ba14274872cde235613723b
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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