Water → HCID 59129745, compound

HRID 1991454Notes

Reaction equation

HRID 1991454 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:13])=[C:8]([OH:12])[C:9]=2[CH3:11])[S:4][C:3]=1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+].Br[CH2:28][CH2:29][Cl:30].O>CC#N>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:13])=[C:8]([O:12][CH2:28][CH2:29][Cl:30])[C:9]=2[CH3:11])[S:4][C:3]=1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 59129736HCID 59129736, compound

Product 1

HCID 59129745HCID 59129745, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The tert-butyl 3-amino-5-hydroxy-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate obtained above (12 g, 40 mmol) was dissolved in CH3CN (300 mL), followed by the addition of K2CO3 (11 g, 80 mmol) and 1-bromo-2-chloroethane (5.7 g, 40 mmol). The mixture was heated to reflux for 8 h, water (100 mL) was added and the mixture was extracted with ethyl acetate (60 mLx 3). The organic layers were washed with 0.5% aqueous sodium hydroxide (150 mL) and brine, dried over anhydrous Na2SO4 and then concentrated to give tert-butyl 3-amino-5-(2-chloroethoxy)-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate as a yellow solid (6.9 g, 50%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 h
  3. extractionthe mixture was extracted with ethyl acetate (60 mLx 3)
  4. washThe organic layers were washed with 0.5% aqueous sodium hydroxide (150 mL) and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-db516b8c949447b8b6ad4fe17035c706
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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