Ethyl Bromide → 5-(4-Ethoxy-5-iodo-2-isopropyl-phenoxy)-pyrimidine-2,4-diamine

HRID 38407Notes

Reaction equation

HRID 38407 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:13]([OH:19])=[C:12]([I:20])[CH:11]=2)=[CH:4][N:3]=1.[CH2:21](Br)[CH3:22]>CN(C=O)C>[CH2:21]([O:19][C:13]1[C:12]([I:20])=[CH:11][C:10]([O:9][C:5]2[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=2)=[C:15]([CH:16]([CH3:18])[CH3:17])[CH:14]=1)[CH3:22]

Participants

4

Reactant 2

HCID 6332Ethyl BromideHCID 159538644-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol

Product 1

HCID 573296125-(4-Ethoxy-5-iodo-2-isopropyl-phenoxy)-pyrimidine-2,4-diamineYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol (0.2 g, 0.52 mmol) in anhydrous DMF (2 ml) was added EtBr (57 mg, 0.52 mmol) in portions. The reaction mixture was partitioned between EtOAc and H2O. The organic extract was dried over Na2SO4, filtered and aconcentrated. Flash chromatography on silica (3% MeOH in methylene chloride with 1% NH4OH) gave 5-(4-Ethoxy-5-iodo-2-isopropyl-phenoxy)-pyrimidine-2,4-diamine (0.17 g, 28%) as a yellow solid. (M+H)=415.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a4f5717cb5c343979f87123a9d74984d
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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