{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-((E)-3-Amino-3-methyl-but-1-enyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HRID 1434951Notes

Reaction equation

HRID 1434951 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.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:2]([CH3:28])([CH3:27])/[CH:3]=[CH: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 2

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)-amineHCID 21226445Aluminium lithium hydride

Product 1

HCID 11304118{4-[5-((E)-3-Amino-3-methyl-but-1-enyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {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 10 ml of THF and LAH (1M in THF, 0.25 ml, 0.25 mmol) was refluxed for 3 hours, poured on water and extracted 3 times with TBME. The combined organic phases were dried over sodium sulfate, filtered and purified via chromatography on silicagel (DCM/MeOH/ammonia:90/10/1 to 85/15/2) to give the title compound as yellow solid. Yield: 20 mg (20%).

Workup

  1. additionpoured on water
  2. extractionextracted 3 times with TBME
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. custompurified via chromatography on silicagel (DCM/MeOH/ammonia:90/10/1 to 85/15/2)

Sources & evidence

ORD record
ord-4e7ddbb05875409bb7f5df479494d9be
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

Loading…