Pentylamine → 6-Methyl-N4-pentyl-5-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)pyrimidine-2,4-diamine
Reaction equation
CC1C=C(C)C=C(C)C=1S(O[C:14]1[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)=[CH:23][CH:22]=2)=[C:18]([CH3:35])[N:17]=[C:16]([NH2:36])[N:15]=1)(=O)=O.[CH2:37]([NH2:42])[CH2:38][CH2:39][CH2:40][CH3:41]>C(O)CCC>[CH3:35][C:18]1[N:17]=[C:16]([NH2:36])[N:15]=[C:14]([NH:42][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:19]=1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)=[CH:25][CH:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of the product from step (iii) (6.49 g) and n-pentylamine (7.34 ml) in 1-butanol was heated under reflux for 24 h. The solvent was evaporated and the residue partitioned between EtOAc and water. The organics were separated, dried and evaporated under reduced pressure. The residue was purified by column chromatography eluting with 8% MeOH/DCM to afford the subtitle compound, 3.4 g.