HCID 86618382, compound → HCID 86618383, compound

HRID 2262074Notes

Reaction equation

HRID 2262074 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]=[CH:6][C:7]1[S:15][C:14]2[C:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[N:12][C:11]([Cl:22])=[N:10][C:9]=2[CH:8]=1)[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[S:15][C:14]2[C:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[N:12][C:11]([Cl:22])=[N:10][C:9]=2[CH:8]=1)[CH3:2]

Participants

5

Reactant 1

HCID 86618382HCID 86618382, compound

Product 1

HCID 86618383HCID 86618383, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To as solution of 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-acrylic acid ethyl ester (2 g) in ethyl acetate (100 mL) was added a suspension of Pd/C (200 mg) in ethanol (10 mL). The flask was flushed with nitrogen and then a hydrogen balloon was fitted. The reaction mixture was stirred at room temperature for 16 h. The mixture was then filtered through Celite and the filtrate concentrated to give 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)propionic acid ethyl ester as a yellow solid (1.83 g).

Workup

  1. customThe flask was flushed with nitrogen
  2. customa hydrogen balloon was fitted
  3. filtrationThe mixture was then filtered through Celite
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-2aa911c13c8040009a938c2d08201263
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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