5-[5-Iodo-2-isopropyl-4-(2-trimethylsilanyloxy-ethoxy)-phenoxy]-pyrimidine-2,4-diamine → 2-[4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenoxy]-ethanol

HRID 1677318Notes

Reaction equation

HRID 1677318 reaction equation
[I:1][C:2]1[C:3]([O:20][CH2:21][CH2:22][O:23][Si](C)(C)C)=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1>CC(O)=O.C1COCC1.O>[NH2:14][C:11]1[N:10]=[C:9]([NH2:15])[C:8]([O:7][C:6]2[C:5]([CH:17]([CH3:18])[CH3:19])=[CH:4][C:3]([O:20][CH2:21][CH2:22][OH:23])=[C:2]([I:1])[CH:16]=2)=[CH:13][N:12]=1

Participants

3

Reactant 1

HCID 595986765-[5-Iodo-2-isopropyl-4-(2-trimethylsilanyloxy-ethoxy)-phenoxy]-pyrimidine-2,4-diamine

Product 1

HCID 573291112-[4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenoxy]-ethanolYield 86%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

5-[5-Iodo-2-isopropyl-4-(2-trimethylsilanyloxy-ethoxy)-phenoxy]-pyrimidine-2,4-diamine (0.38 g, 0.69 mmol) in a solution of HOAc/THF/H2O in a ratio of 3:1:1.95 ml) was heated at 65° C. for 16 hrs. The pH of the reaction mixture was adjusted to pH=9 and extracted into methylene chloride. The combined extracts was dried over Na2SO4, filtered and concentrated. Flash chromatography on silica (5% MeOH in methylene chloride with 0.1% NH4OH) gave 2-[4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenoxy]-ethanol (0.25 g, 86%) as a white solid. (M+H)=431

Workup

  1. extractionextracted into methylene chloride
  2. dry with materialThe combined extracts was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-13d20adee720481fbf647a485131dacd
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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