1-[N-(2-cyanoethyl)tetradecanamido]-5-(4,6-dimethyl-2-pyrimidylamino)-pentane → 1-[N-(3-aminopropyl)tetradecanamido]-5-(4,6-dimethyl-2-pyrimidylamino)pentane

HRID 34755Notes

Reaction equation

HRID 34755 reaction equation
[C:1]([CH2:3][CH2:4][N:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]1[N:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[N:28]=1)[C:6](=[O:20])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])#[N:2]>N.C(O)C.[Rh]>[NH2:2][CH2:1][CH2:3][CH2:4][N:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]1[N:28]=[C:29]([CH3:34])[CH:30]=[C:31]([CH3:33])[N:32]=1)[C:6](=[O:20])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 1

HCID 143460191-[N-(2-cyanoethyl)tetradecanamido]-5-(4,6-dimethyl-2-pyrimidylamino)-pentane

Product 1

HCID 143460201-[N-(3-aminopropyl)tetradecanamido]-5-(4,6-dimethyl-2-pyrimidylamino)pentane

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

The nitrile (XIV) (330 mg) was dissolved in 5 ml of 10% conc. NH3 in ethanol to which was added a spatula tip full of 5% Rh on alumina. After 5 hours stirring under 1 atm H2, there was no reaction indicated by tlc or H2 uptake. Additional catalyst (about 2×) and solvent were added and the hydrogenation continued overnight. The catalyst was filtered off and the solvents removed under vacuum to yield the product XV.

Workup

  1. additionAdditional catalyst (about 2×) and solvent were added
  2. waitthe hydrogenation continued overnight
  3. filtrationThe catalyst was filtered off
  4. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-6893e3738b5e482da2d5cb4721051e88
Source dataset
uspto-grants-1988_08
Patent number
US04762949

Reaction notes

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