Hydrochloric Acid → [2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol

HRID 1508714Notes

Reaction equation

HRID 1508714 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([CH3:20])[N:15]=[C:14]([C:21]3[S:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[N:13]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([CH3:20])[N:15]=[C:14]([C:21]3[S:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[N:13]=2)=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 901105222-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]benzoic acid

Product 1

HCID 90112603[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanolYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 100-mL round bottomed flask was charged with 2-bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]benzoic acid (impure, obtained from several reactions on 1.3 mmol scale), THF (20 ml). To the mixture was added BH3 (1N in THF, 7.5 ml). The resulting mixture was stirred at rt overnight. Then treated with 2N HCl aq. (10 ml) followed by sodium bicarbonate to pH=7. The mixture was extracted with ethyl acetate (3×10 ml). The organic layers were combined and dried over Na2SO4. Removal of solvent gave a residue, which was purified by chromatography on silica gel using 0.5% of methanol in dichloromethane to give the title compound (198 mg, 35% yield).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
  2. dry with materialdried over Na2SO4
  3. customRemoval of solvent
  4. customgave a residue, which
  5. customwas purified by chromatography on silica gel using 0.5% of methanol in dichloromethane

Sources & evidence

ORD record
ord-391e18d601754b75986303392d94a40a
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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