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

HRID 34754

Reaction equation

HRID 34754 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[N:13]=1)#[N:2].[C:20](Cl)(=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>N1C=CC=CC=1>[C:1]([CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[N:17]=1)[C:20](=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])#[N:2]

Participants

4

Reactant 2

HCID 66986Myristoyl chlorideHCID 143460181-(2-Cyanoethylamino)-5-(4,6-dimethyl-2-pyrimidylamino)pentane

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Crude XIII was dissolved in dry pyridine to which 1 eq of tetradecanoyl chloride was added with stirring. The run was followed by tlc and excess acid chloride was added to drive the reaction to completion. Ice was then added to quench the reaction followed by the addition of CHCl3. The mixture was first extracted with 10% NaHCO3 and then with 1M HOAc to remove the bulk of the pyridine. The remaining CHCl3 phase was evaporated to yield the crude product which was purified by chromatography on a 100 g silica gel (Brinkman 50-200μ) column developed with 30% acetone/chloroform. The product (1 g) was collected after only 150 ml of eluant had passed through the column and was only partially purified.

Workup

  1. additionwas added
  2. additionwas added
  3. customthe reaction to completion
  4. additionIce was then added
  5. customto quench the reaction
  6. additionfollowed by the addition of CHCl3
  7. extractionThe mixture was first extracted with 10% NaHCO3
  8. customwith 1M HOAc to remove the bulk of the pyridine
  9. customThe remaining CHCl3 phase was evaporated

Sources & evidence

ORD record
ord-c8bf72232d3b47c7a1a782d5442b0f34
Source dataset
uspto-grants-1988_08
Patent number
US04762949

Linked notes

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