Diisopropylethylamine → HCID 86680939, compound

HRID 2365450Notes

Reaction equation

HRID 2365450 reaction equation
CS([C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:14][CH:13]=2)[CH:8]=[C:7]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[N:6]=1)(=O)=O.CCN(C(C)C)C(C)C.[NH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=1>C1COCC1>[OH:48][C:45]1[CH:46]=[CH:47][C:42]([CH2:41][NH:40][C:5]2[N:10]=[C:9]([NH:11][C:12]3[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:14][CH:13]=3)[CH:8]=[C:7]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[N:6]=2)=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 974724-HydroxybenzylamineHCID 86680940HCID 86680940, compound

Product 1

HCID 86680939HCID 86680939, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-((2-(methylsulfonyl)-6-(2,2,2-trifluoroethoxy)pyrimidin-4-yl)amino)benzoate (80 mg, 0.18 mmol), and Hunig's Base (0.062 mL, 0.36 mmol) in THF (1 mL) was added 4-(aminomethyl)phenol (44 mg, 0.36 mmol). The resulting mixture was stirred at r.t for 16 hs. The solvent was removed and the crude product was purified by silica gel chromatography using 40-70%-100% EtOAc/Hexanes to give tert-butyl 4-((2-((4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)pyrimidin-4-yl)amino)benzoate (72 mg, 83%) as white solid.

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-08fc26ff12a64f0c8c07e918da47bb94
Source dataset
uspto-grants-2014_04
Patent number
US08697706B2

Reaction notes

Loading…