Sodium Cyanide → HCID 24855098, compound

HRID 1689937Notes

Reaction equation

HRID 1689937 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[S:23][CH:22]=[CH:21][C:10]=3[N:11]=[C:12]([C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)[N:13]=2)[CH:5]=[CH:4][N:3]=1.[C-]#N.[Na+].[CH3:27][N:28]1C(=O)CCC1>O.[Ni](Br)Br>[OH:20][C:16]1[CH:15]=[C:14]([C:12]2[N:13]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:27]#[N:28])[CH:7]=3)[C:9]3[S:23][CH:22]=[CH:21][C:10]=3[N:11]=2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 13387N-methyl-2-pyrrolidoneHCID 24855096HCID 24855096, compound

Product 1

HCID 24855098HCID 24855098, compound

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 3-[4-(2-chloro-pyridin-4-yl)-thieno[3,2-d]pyrimidin-2-yl]-phenol (90 mg), sodium cyanide (26 mg), nickel (II) bromide (58 mg) and NMP was heated under microwave irradiation at 200° C. for 30 minutes. The mixture was cooled, diluted with water and the precipitate collected by filtration. The title compound was isolated following flash column chromatography (31 mg).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-29d3becf930648e58e529707b7e6d389
Source dataset
uspto-grants-2012_04
Patent number
US08153639B2

Reaction notes

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