Water → HCID 57753035, compound

HRID 225450Notes

Reaction equation

HRID 225450 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:13]3[N:14]=[C:15]([CH3:28])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]4)[C:12]=3[S:11][C:10]=2[CH3:29])=[C:4]([CH3:30])[CH:3]=1.I[CH2:32][CH3:33].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH2:32]([O:26][C:25](=[O:27])[CH2:24][CH:21]1[CH2:20][CH2:19][N:18]([C:17]2[C:12]3[S:11][C:10]([CH3:29])=[C:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=4[CH3:30])[C:13]=3[N:14]=[C:15]([CH3:28])[N:16]=2)[CH2:23][CH2:22]1)[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 57753033HCID 57753033, compound

Product 1

HCID 57753035HCID 57753035, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidin-4-yl}-acetic acid (30 mg), iodoethane (97 mg) and K2CO3 (17 mg) in DMF (1 mL) was stirred at room temperature for 16 hours. To the reaction mixture were added H2O and EtOAc and separated. The organic layer washed brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: Hexane/EtOAc=4:1) to obtain the title compound (22 mg) as a white crystal.

Workup

  1. customseparated
  2. washThe organic layer washed brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: Hexane/EtOAc=4:1)

Sources & evidence

ORD record
ord-21b3d4ff1c5543f89361f294cc4edd60
Source dataset
uspto-grants-2009_07
Patent number
US07557111B2

Reaction notes

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