Pentylamine → 6-Methyl-N4-pentyl-5-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)pyrimidine-2,4-diamine

HRID 1617188Notes

Reaction equation

HRID 1617188 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]=1

Participants

4

Reactant 2

HCID 8060PentylamineHCID 866768952-Amino-6-methyl-5-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)pyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 684154226-Methyl-N4-pentyl-5-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. customThe solvent was evaporated
  4. customthe residue partitioned between EtOAc and water
  5. customThe organics were separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluting with 8% MeOH/DCM

Sources & evidence

ORD record
ord-749af9b865034e809959c7f94fb35932
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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