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

HRID 2387824Notes

Reaction equation

HRID 2387824 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-7d6450b305004c2fa1b3fa351c60f551
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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