Hydrochloric Acid → HCID 66958235, compound

HRID 1912650Notes

Reaction equation

HRID 1912650 reaction equation
Cl[C:2]1[C:7]([O:8]C)=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1.C1N2CC[N:19](CC2)[CH2:18]1.[C-]#N.[K+].Cl>CN(C=O)C.ClCCl.CN1C(=O)CCC1>[OH:8][C:7]1[C:2]([C:18]#[N:19])=[N:3][CH:4]=[N:5][C:6]=1[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 9237DabcoHCID 81724702HCID 81724702, compound

Product 1

HCID 66958235HCID 66958235, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-chloro-5-methoxy-6-p-tolylpyrimidine P5 (100 mg, 0.43 mmol) in DMF (2 mL) and NMP (0.5 mL) was added triethylenediamine (62 mg, 0.55 mmol) and potassium cyanide (55 mg, 0.85 mmol). The reaction mixture was stirred at room temperature for 18 hours. Dichloromethane and 1 N hydrochloric acid were added. The organic layer was dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to afford the desired 5-hydroxy-6-p-tolylpyrimidine-4-carbonitrile P69 (70 mg, 0.33 mmol).

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. customThe organic solvent was evaporated under reduced pressure
  3. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-16918a7772d74edb91d90c4151748917
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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