Phosphorus oxychloride → 5-Methyl-2-(methylthio)-7-phenylimidazo[5,1-F][1,2,4]triazine

HRID 2375010Notes

Reaction equation

HRID 2375010 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]([CH:9]([NH:11][C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:10])=[CH:7][N:8]=1.P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:10][C:9]1[N:11]=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]2[C:6]=1[CH:7]=[N:8][C:3]([S:2][CH3:1])=[N:4]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58711952HCID 58711952, compound2×

Product 1

HCID 534718325-Methyl-2-(methylthio)-7-phenylimidazo[5,1-F][1,2,4]triazineYield 63.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, using N-{1-[3-(methylthio)-1,2,4-triazin-6-yl]ethyl}benzamide (Intermediate 70) (590 mg, 2.15 mmol), 1,2-dichloroethane (10 mL) and phosphorus oxychloride (1.60 mL, 17.17 mmol), to afford 5-methyl-2-(methylthio)-7-phenylimidazo[5,1-f][1,2,4]triazine (350 mg) as a yellow solid. MS m/z 257 (M+1).

Sources & evidence

ORD record
ord-845922fe9d5445cab18b518485dac14a
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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