HCID 117778962, compound → HCID 117779063, compound

HRID 2206646Notes

Reaction equation

HRID 2206646 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([N:16]2[C:20]3[N:21]=[C:22](Cl)[N:23]=[CH:24][C:19]=3[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:17]2[CH3:31])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([N:16]2[C:20]3[N:21]=[CH:22][N:23]=[CH:24][C:19]=3[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:17]2[CH3:31])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 117778962HCID 117778962, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117779063HCID 117779063, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound ethyl 7-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethyl)-2-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (75 mg, 0.16 mmol) and Pd/C (10 mg) in methanol (10 mL) was stirred under 50 psi of hydrogen at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated to give product ethyl 7-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethyl)-6-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (50 mg, yield: 72%). LRMS (M+H+) m/z: calcd 450.2. found 451.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-575a4c0a02cb4b56a59fe05c6a545ec8
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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