Ethanol → HCID 86690167, compound

HRID 336364Notes

Reaction equation

HRID 336364 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3S[CH2:22][CH2:21][C:16]=3[N:17]=[C:18]([Cl:20])[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C.[H][H]>C1COCC1.C(N(CC)CC)C.[Pd].[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([CH2:21][CH3:22])[N:17]=[C:18]([Cl:20])[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 702EthanolHCID 86686508HCID 86686508, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86690167HCID 86690167, compoundYield 10.9%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

200 mg palladium charcoal was added to 200 mg 4-(2-chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester in 10 mL THF and 0.08 mL triethylamine. Raney-nickel and 5 mL ethanol was added and the reaction was stirred 24 h at 50° C. and 3 bar hydrogen. The mixture was filtered. The filtrate was evaporated and the residue was purified by HPLC to give 20 mg desired product.

Workup

  1. filtrationThe mixture was filtered
  2. customThe filtrate was evaporated
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-d2ae3bcd24ec45b7a00e85d5ca551dac
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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