Methyl bromoacetate → Methyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenoxy)acetate

HRID 1617202Notes

Reaction equation

HRID 1617202 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[NH2:7][C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=2[O:23][CH3:24])=[C:10]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:9]=1>CN(C=O)C>[NH2:7][C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:18][C:17]=2[O:23][CH3:24])=[C:10]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:9]=1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 684158324-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenol

Product 1

HCID 42613315Methyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl bromoacetate (57 ul) was added to a mixture of the product from step (v) (0.2 g) and K2 CO3 (0.251 g) in DMF (10 ml) and the mixture stirred at rt for 24 h. The mixture was partitioned between EtOAc/water, the organics separated, dried and evaporated under reduced pressure. The residue was purified by RPHPLC to afford the title compound, 0.057 g

Workup

  1. customThe mixture was partitioned between EtOAc/water
  2. customthe organics separated, dried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-e91e9884ae3c45b29a3396f74348e53f
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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