Pyridine → HCID 178514143, compound

HRID 393183Notes

Reaction equation

HRID 393183 reaction equation
[NH2:1][C:2]1[NH:7][C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:5][C:4](=[O:16])[CH:3]=1.[S-:17][C:18]#[N:19].[K+].N1C=CC=CC=1.BrBr>CN(C)C=O.O>[NH2:1][C:2]1[NH:7][C:6]([S:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:5][C:4](=[O:16])[C:3]=1[S:17][C:18]#[N:19]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 178507956HCID 178507956, compound

Product 1

HCID 178514143HCID 178514143, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

6-Amino-2-[(phenylmethyl)thio]-4-(1H)-pyrimidinone (10.5 g) (prepared as described in WO 96/35678) and potassium thiocyanate (25 g) in dimethylformamide (200 mL) were heated together at 65° C. Pyridine (6.3 mL) was added and the solution cooled to 5° C. Bromine (2.2 mL) was added slowly and the reaction mixture stirred for 2 hours at 5-10° C. The reaction mixture was poured onto ice and water, stirred for 1 hour and the solid was filtered off. After washing with water and ether a pure sample was obtained after tituration with hot methanol.

Workup

  1. stirringstirred for 1 hour
  2. filtrationthe solid was filtered off
  3. washAfter washing with water and ether a pure sample
  4. customwas obtained after tituration with hot methanol

Sources & evidence

ORD record
ord-462e8151525145b38a104773e90db19c
Source dataset
uspto-grants-2004_10
Patent number
US06806273B1

Reaction notes

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