Trifluoroacetic acid → 5-(3-Aminopropyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

HRID 1617123Notes

Reaction equation

HRID 1617123 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[C:4]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:12][CH2:11][CH2:10][CH2:9][C:5]1[C:4]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[N:3][C:2]([NH2:1])=[N:7][C:6]=1[CH3:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86633392tert-Butyl 3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylcarbamate

Product 1

HCID 98378705-(3-Aminopropyl)-6-methyl-N4-pentylpyrimidine-2,4-diamineYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (iv) (3.8 g) was dissolved in DCM (100 mL) and TFA (35 mL) and the reaction mixture stirred at rt for 16 h. The solvent was evaporated and the residue taken up in MeOH. The product was purified via SCX resin to give the subtitle compound 2.3 g.

Workup

  1. customThe solvent was evaporated
  2. customThe product was purified via SCX resin

Sources & evidence

ORD record
ord-6223fbed4dd548d38224e306f12a9cb3
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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