Pentylamine → 4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenol

HRID 1617201Notes

Reaction equation

HRID 1617201 reaction equation
CC1C=C(C)C=C(C)C=1S([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[C:22](OS(C3C(C)=CC(C)=CC=3C)(=O)=O)=[N:23][C:24]([NH2:28])=[N:25][C:26]=2[CH3:27])=[C:16]([O:42][CH3:43])[CH:15]=1)(=O)=O.[CH2:44]([NH2:49])[CH2:45][CH2:46][CH2:47][CH3:48]>O1CCOCC1>[NH2:28][C:24]1[N:25]=[C:26]([CH3:27])[C:21]([CH2:20][C:17]2[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][C:16]=2[O:42][CH3:43])=[C:22]([NH:49][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[N:23]=1

Participants

4

Reactant 2

HCID 8060PentylamineHCID 866334084-((2-Amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 684158324-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product from step (iv) (9.51 g) and pentylamine (12 ml) in dioxane (100 ml) was heated under reflux for 48 h. The solvent was evaporated and the residue partitioned between EtOAc/water. The organics were separated, washed with aq NaHCO3 soln, water, dried and evaporated under reduced pressure. The residue was dissolved in MeOH (200 ml) then aq NaOH (2M, 40 ml) added and the mixture heated under reflux for 6 h. The mixture was acidified to pH 7 with aq 2M HCl, the solvent evaporated under reduced pressure and the residue partitioned between DCM/water. The organics were separated, washed with aq NaHCO3 soln, brine, dried and evaporated under reduced pressure. The residue was triturated with ethyl acetate and filtered to afford the subtitle compound, 2.43 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. customThe solvent was evaporated
  4. customthe residue partitioned between EtOAc/water
  5. customThe organics were separated
  6. washwashed with aq NaHCO3 soln
  7. dry with materialwater, dried
  8. customevaporated under reduced pressure
  9. dissolutionThe residue was dissolved in MeOH (200 ml)
  10. additionaq NaOH (2M, 40 ml) added
  11. temperaturethe mixture heated
  12. temperatureunder reflux for 6 h
  13. customthe solvent evaporated under reduced pressure
  14. customthe residue partitioned between DCM/water
  15. customThe organics were separated
  16. washwashed with aq NaHCO3 soln
  17. dry with materialbrine, dried
  18. customevaporated under reduced pressure
  19. customThe residue was triturated with ethyl acetate
  20. filtrationfiltered

Sources & evidence

ORD record
ord-f879cf6dfe034bd2b3c68e47d328e179
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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