Pyridine → HCID 178514143, compound

HRID 1097322Notes

Reaction equation

HRID 1097322 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>[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

6

Reactant 4

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

Product 1

HCID 178514143HCID 178514143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

6-Amino-2-[(phenylmethyl)thio]-4(1H)-pyrimidinone (10.5 g)[preparation as described in WO 9635678] and potassium thiocyanate (25 g) in N,N-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 water, stirred for 1 hour and the solid was isolated by filtration. After washing with water and ether, a pure sample was obtained after trituration with hot methanol.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. stirringstirred for 1 hour
  3. customthe solid was isolated by filtration
  4. washAfter washing with water and ether
  5. customa pure sample was obtained after trituration with hot methanol

Sources & evidence

ORD record
ord-5841e042ad2744af819264a73295d587
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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