Methyl 2-(3-formylphenoxy)acetate → Methyl 2-(3-((3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenoxy)acetate

HRID 1617170Notes

Reaction equation

HRID 1617170 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:22]=[C:23]([CH:30]=[CH:31][CH:32]=1)[O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=O>C1COCC1.[BH4-].[Na+]>[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]=[C:23]([CH:30]=[CH:31][CH:32]=2)[O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[C:6]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:7]=1

Participants

5

Reactant 2

HCID 1494380Methyl 2-(3-formylphenoxy)acetateHCID 98378705-(3-Aminopropyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Product 1

HCID 42613155Methyl 2-(3-((3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenoxy)acetateYield 11.2%

Reagents, catalysts & solvents 2

HCID 4311764Sodium borohydrideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product from example 1 step (v) (0.2 g) was dissolved in THF (10 mL) then methyl 2-(3-formylphenoxy)acetate (0.154 g) was added and stirred at rt overnight. Sodium borohydride (0.0301 mg) was added and stirred for 3 hr. The reaction was quenched with water and extracted with EtOAc, dried and solvent removed under reduced pressure. The residue was purified by RPHPLC to afford the title compound 0.038 g.

Workup

  1. stirringstirred for 3 hr
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customdried
  5. customsolvent removed under reduced pressure
  6. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-89c9501ac1d14b7c9f3aef099ffcf1d6
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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