Acetic Acid → Methyl 2-(4-((3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetate

HRID 1617125Notes

Reaction equation

HRID 1617125 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[N:7][C:8]([NH2:12])=[N:9][C:10]=1[CH3:11].[CH:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=1)=O.C(O)(=O)C.[BH4-].[Na+]>C1COCC1.CO>[NH2:12][C:8]1[N:9]=[C:10]([CH3:11])[C:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:19][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:26]=2)=[C:6]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 98378705-(3-Aminopropyl)-6-methyl-N4-pentylpyrimidine-2,4-diamineHCID 19363032Methyl 2-(4-formylphenyl)acetate

Product 1

HCID 42613958Methyl 2-(4-((3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetateYield 60.8%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 1 step (v) (0.3 g) and methyl 2-(4-formylphenyl)acetate (0.213 g) were combined in THF (20 mL), acetic acid (0.072 g) was added and the reaction mixture stirred at rt for 16 h. Sodium borohydride (0.0677 g) and MeOH (3 drops) were added and the reaction mixture stirred for 72 h. The solvents were evaporated and the product dissolved in MeOH and purified by RPHPLC to give the title compound 0.3 g.

Workup

  1. stirringthe reaction mixture stirred for 72 h
  2. customThe solvents were evaporated
  3. dissolutionthe product dissolved in MeOH
  4. custompurified by RPHPLC

Sources & evidence

ORD record
ord-3193e7183a6e411690e9ed6d6296e16c
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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