Dimethylformamide → HCID 67452356, compound

HRID 2276784Notes

Reaction equation

HRID 2276784 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[N:12]=[N:11][C:10]([NH2:13])=[N:9][CH:8]=2)=[N:4][CH:3]=1.[CH3:14][N:15](C=O)C>C(Cl)Cl.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:13][C:10]1[N:11]=[N:12][C:7]([C:5]2[S:6][C:2]([C:14]#[N:15])=[CH:3][N:4]=2)=[CH:8][N:9]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 67454721HCID 67454721, compound

Product 1

HCID 67452356HCID 67452356, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

6-(5-Bromothiazol-2-yl)-1,2,4-triazin-3-amine (300 mg, 1.15 mmol), zinc cyanide (340 mg, 2.30 mmol), Pd(PPh3)4 (133 mg, 0.13 mmol), and DMF (5 mL) were combined and heated to 160° C. for 12 h. The reaction mixture was cooled, diluted with CH2Cl2 (30 mL), filtered through silica gel, eluted with EtOAc, and concentrated. The crude product was then purified using silica gel chromatography to afford 30 mg of 2-(3-amino-1,2,4-triazin-6-yl)thiazole-5-carbonitrile.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through silica gel
  3. washeluted with EtOAc
  4. concentrationconcentrated
  5. customThe crude product was then purified

Sources & evidence

ORD record
ord-cf85f7ec7b8541f6923146af1fa15785
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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