HCID 22249265, compound → HCID 22249256, compound

HRID 557375Notes

Reaction equation

HRID 557375 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:14]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[N:15][C:16](SC)=[N:17][CH:18]=2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>CCO.[Ni]>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2[C:14]([NH:21][CH2:22][C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)=[N:15][CH:16]=[N:17][CH:18]=2)=[O:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22249265HCID 22249265, compound

Product 1

HCID 22249256HCID 22249256, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[4-(isopropyl)phenyl]{2-methylthio-4-[(4-pyridylmethyl)amino]pyrimidin-5-yl}carboxamide (50 mg, 0.13 mmol, Step B) and Raney-Ni in EtOH (10 mL) was heated at reflux for 2 h. The resulting mixture was filtered, and the filtrate was concentrated to give the titled compound. MS (ES+): 348 (M+H)+; (ES−): 346 (M−H)−. Calc'd C20H21N5O−347.42.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5dc66b79d94d40f894751be829dd43d6
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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