Water → HCID 89579329, compound

HRID 928611Notes

Reaction equation

HRID 928611 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]1([C:13]2[C:21]3[C:20]([N:22]4[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][CH:30]5[CH2:33][CH2:32][CH2:31]5)[CH2:24][CH2:23]4)=[N:19][CH:18]=[N:17][C:16]=3[S:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[CH:30]1([N:29]([CH2:28][CH:25]2[CH2:24][CH2:23][N:22]([C:20]3[C:21]4[C:13]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=5)=[CH:14][S:15][C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:27][CH2:26]2)[CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:33][CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 89579835HCID 89579835, compound

Product 1

HCID 89579329HCID 89579329, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl bromoacetate (15 μL, 0.158 mmol) was added dropwise to a stirred suspension of N—[[1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methyl]cyclobutanamine (50 mg, 0.132 mmol) and cesium carbonate (51 mg, 0.158 mmol) in dry DMF (4 mL) at room temperature. The reaction was allowed to stir for 2 h, then water and ethyl acetate were added and the organic layer separated. The aqueous layer was further extracted with ethyl acetate (×3). The organic layers were combined, washed with water, dried by passage through a hydrophobic frit and concentrated in vacuo to give methyl 2-[cyclobutyl-[[1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methyl]amino]acetate as a colourless oil (37 mg). LCMS RT=3.20. M+1=451.

Workup

  1. customthe organic layer separated
  2. extractionThe aqueous layer was further extracted with ethyl acetate (×3)
  3. washwashed with water
  4. customdried by passage through a hydrophobic frit
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-556d0fbf8ea744eea0d14513f1bdce1e
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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